CA2219278A1 - Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid - Google Patents

Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid

Info

Publication number
CA2219278A1
CA2219278A1 CA002219278A CA2219278A CA2219278A1 CA 2219278 A1 CA2219278 A1 CA 2219278A1 CA 002219278 A CA002219278 A CA 002219278A CA 2219278 A CA2219278 A CA 2219278A CA 2219278 A1 CA2219278 A1 CA 2219278A1
Authority
CA
Canada
Prior art keywords
acid
methylhexanoic acid
carbamoylmethyl
aminomethyl
reacting
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002219278A
Other languages
French (fr)
Other versions
CA2219278C (en
Inventor
Brian Keith Huckabee
Denis Martin Sobieray
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Warner Lambert Co LLC
Original Assignee
Warner-Lambert Company
Brian Keith Huckabee
Denis Martin Sobieray
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US08/458,950 external-priority patent/US5616793A/en
Application filed by Warner-Lambert Company, Brian Keith Huckabee, Denis Martin Sobieray filed Critical Warner-Lambert Company
Publication of CA2219278A1 publication Critical patent/CA2219278A1/en
Application granted granted Critical
Publication of CA2219278C publication Critical patent/CA2219278C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Abstract

The present invention provides a method of making (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid which comprises condensing isovaleraldehyde with an alkyl cyanoacetate to form a 2-cyano-5-methylhex-2-enoic acid alkyl ester, reacting the 2-cyano-5-methylhex-2-enoic acid alkyl ester with a dialkyl malonate to form 3-isobutylglutaric acid; forming the anhydride of 3-isobutylglutaric acid;
reacting the anhydride with ammonia to form (~)-3-(carbamoylmethyl)-5-methylhexanoic acid' reacting (t)-3-(carbamoylmethyl)-5-methylhexanoic acid with (R)-(+)-.alpha.-phenylethylamine to obtain the (R)-(+)-.alpha.-phenylethylamine salt of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid;
combining the salt with an acid to obtain (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid' and reacting the (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid with a Hofmann reagent to obtain (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid.
CA002219278A 1995-06-02 1996-04-26 Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid Expired - Fee Related CA2219278C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/458,950 US5616793A (en) 1995-06-02 1995-06-02 Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid
US458,950 1995-06-02
PCT/US1996/005831 WO1996038405A1 (en) 1995-06-02 1996-04-26 Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid

Publications (2)

Publication Number Publication Date
CA2219278A1 true CA2219278A1 (en) 1996-12-05
CA2219278C CA2219278C (en) 2006-06-13

Family

ID=36587392

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002219278A Expired - Fee Related CA2219278C (en) 1995-06-02 1996-04-26 Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid

Country Status (1)

Country Link
CA (1) CA2219278C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109761838A (en) * 2019-02-22 2019-05-17 浙江华海药业股份有限公司 A method of preparing pregabalin intermediate and recycling resolving agent

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109761838A (en) * 2019-02-22 2019-05-17 浙江华海药业股份有限公司 A method of preparing pregabalin intermediate and recycling resolving agent

Also Published As

Publication number Publication date
CA2219278C (en) 2006-06-13

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