Patents Assigned to Aldrich Chemical Company, Inc.
  • Dioxane-monochloroborane and dioxane-dichloroborane
    Patent number: 6008414
    Abstract: Highly reactive hydroborating agents dioxane-monochloroborane and dioxane-dichloroborane are provided. Also provided by this invention are methods for producing dioxane-monochloroborane, dioxane-dichloroborane and methods for hydroborating olefins with these reagents.
    Type: Grant
    Filed: February 16, 1999
    Date of Patent: December 28, 1999
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Borane-sulfide hydroboration agents
    Patent number: 5567849
    Abstract: A borane-sulfide represented by the formulaBH.sub.3.SR.sup.1 R.sup.2wherein B is boron, H is hydrogen, R.sup.1 and R.sup.2 each are straight or branched chain alkyl or alkoxy with at least one R being a branched chain when both R.sup.1 and R.sup.2 are alkyl, and S is sulfur. The compounds are hydroboration agents.
    Type: Grant
    Filed: May 9, 1995
    Date of Patent: October 22, 1996
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Dicyclooctylhaloboranes
    Patent number: 5552081
    Abstract: A novel class of enolboration reagents represented by the formulaR.sub.2 BX/R'.sub.3 Nwherein each R is the same or different alkyl or cycloalkyl, B is boron, X is halo, R' is lower alkyl and/indicates that R.sub.2 BX is preferably employed in the presence of R'.sub.3 N are disclosed. Methods of enolborating a wide variety of organic carbonyl compounds are also provided.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: September 3, 1996
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Borane-N,N-dialkylaniline hydroboration agents
    Patent number: 5543569
    Abstract: Borane-N,N-dialkylanilines represented by the formulaH.sub.3 B. C.sub.6 H.sub.5 NRR'wherein N is nitrogen, R is isobutyl or isopropyl and R' is straight or branched chain lower alkyl. The compounds are useful as hydroboration agents and for generating diborane.
    Type: Grant
    Filed: May 9, 1995
    Date of Patent: August 6, 1996
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Borane-hydroxydialkylsulfide borates
    Patent number: 5504240
    Abstract: Novel borane adducts of hydroxydialkylsulfide borate esters represented by formula ##STR1## wherein R is straight or branched chain alkyl or alkoxy having from 2 to 5 carbon atoms and n is 1 to 3 inclusive. The compound are new hydroboration agents.
    Type: Grant
    Filed: May 9, 1995
    Date of Patent: April 2, 1996
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Borane-N,N-diisopropylalkylamine hydroboration agents
    Patent number: 5481038
    Abstract: Borane-N,N-diisopropylalkylamines as represented by the formula:H.sub.3 B.NPr.sup.i.sub.2 Rwherein Pr.sup.i is isopropyl, R is branched-chain alkyl or cycloalkyl having 3 to 6 carbon atoms and B is boron are provided. The compounds are new hydroboration agents.
    Type: Grant
    Filed: May 9, 1995
    Date of Patent: January 2, 1996
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Bis(bicyclo(2.2.2)octyl)haloboranes
    Patent number: 5380940
    Abstract: A novel class of enolboration reagents represented by the formulaR.sub.2 BX/R'.sub.3 Nwherein each R is the same or different alkyl or cycloalkyl, B is boron, X is halo, R' is lower alkyl and / indicates that R.sub.2 BX is preferably employed in the presence of R'.sub.3 N are disclosed. Methods of enolborating a wide variety of organic carbonyl compounds are also provided. Further, new bis(bicyclo[2.2.2.]octyl)haloboranes are efficacious for enolboration.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: January 10, 1995
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Method of producing primary amines in high yields
    Patent number: 5284976
    Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group. attached to boron, B is boron and Me is methyl.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: February 8, 1994
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Process for producing dimethylorganoboranes
    Patent number: 5276195
    Abstract: A process for preparing a dimethylorganoborane represented by the formula R*BMe.sub.2 wherein R* is a chiral organyl group attached to the boron, B is boron and Me is methyl comprising treating a chiral boronic ester R*B(OR').sub.2 with a methyl magnesium salt or trimethylaluminum wherein R* is the same chiral organyl group and R' is alkyl.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: January 4, 1994
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Method of producing primary amines in high yields and novel intermediates therefor
    Patent number: 5214209
    Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group,attached to boron, B is boron and Me is methyl.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: May 25, 1993
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Process for producing optically active alcohols
    Patent number: 5202502
    Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo, and a process of using such for the production of optically active alcohols.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: April 13, 1993
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Synthesis of optically pure forms of ipsdienol
    Patent number: 5175378
    Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: December 29, 1992
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Synthesis of optically pure forms of ipsenol
    Patent number: 5175371
    Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: December 29, 1992
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Chemically and optically pure B-halodiiso-2-ethylapopinocampheylboranes
    Patent number: 5159116
    Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by ##STR1## wherein B is borane and X is halo.
    Type: Grant
    Filed: July 15, 1991
    Date of Patent: October 27, 1992
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Intermediates useful for the chiral isoprenylation of aldehydes
    Patent number: 5103063
    Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol. This invention also concerns novel intermediates R'.sub.2 B(2'-isoprenyl) wherein R' is isopinocampheyl, 2-isocaranyl and 4-isocaranyl.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: April 7, 1992
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Method of producing primary amines in high yields
    Patent number: 5087700
    Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group, attached to boron, B is boron and Me is methyl.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: February 11, 1992
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Process for producing optically pure 2-phenoxyphenylalkylamines
    Patent number: 5068432
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: November 26, 1991
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Chemically and optically pure diisopinocampheylhaloboranes
    Patent number: 5043479
    Abstract: Novel chemically pure diisopinocampheylhaloboranes of essentially 100% ee, represented by the formula Ipc.sub.2 BX wherein Ipc is isopinocampheyl and X is halo.
    Type: Grant
    Filed: September 1, 1989
    Date of Patent: August 27, 1991
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Novel .beta.-(2-alkenyl)bis(2-isocaranyl)boranes
    Patent number: 4978794
    Abstract: 2-Alkenylbis(2-isocaranyl)boranes represented by the formula: ##STR1## wherein R is 2-alkenyl. The compounds undergo asymmetric 2-alkenylboration with a variety of aldehydes and afford the corresponding alcohols in 94-99% ee.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: December 18, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Method of producing primary amines in high yields and novel intermediates therefor
    Patent number: 4918229
    Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMBe.sub.2 wherein R is an organo group, R* is a chiral organo group attached to boron, B is boron and Me is methyl.
    Type: Grant
    Filed: July 29, 1988
    Date of Patent: April 17, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown