WO2003018572A1 - 3-(n-alkoxycarbonyl-n-methyl)amino-1-alkoxycarbonyl- oxy-(2-thienyl)propanes and process for preparing 3-(n- methylamino)-1-(2-thienyl)-propan-1-ol with the same - Google Patents

3-(n-alkoxycarbonyl-n-methyl)amino-1-alkoxycarbonyl- oxy-(2-thienyl)propanes and process for preparing 3-(n- methylamino)-1-(2-thienyl)-propan-1-ol with the same Download PDF

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Publication number
WO2003018572A1
WO2003018572A1 PCT/JP2002/008588 JP0208588W WO03018572A1 WO 2003018572 A1 WO2003018572 A1 WO 2003018572A1 JP 0208588 W JP0208588 W JP 0208588W WO 03018572 A1 WO03018572 A1 WO 03018572A1
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WO
WIPO (PCT)
Prior art keywords
thienyl
alkoxycarbonyl
propan
propanes
methylamino
Prior art date
Application number
PCT/JP2002/008588
Other languages
French (fr)
Japanese (ja)
Inventor
Masaya Ikunaka
Jun Matsumoto
Toru Inoue
Original Assignee
Nagase & Co., Ltd.
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
Application filed by Nagase & Co., Ltd. filed Critical Nagase & Co., Ltd.
Publication of WO2003018572A1 publication Critical patent/WO2003018572A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Optically active 3-(N-alkoxycarbonyl-N-methyl)amino-1- alkoxycarbonyloxy-(2-thienyl)propanes, which are novel compounds of the general formula (I), can be prepared by reacting optically active 3-(N,N-dimethylamino)-1-(2-thienyl)-propan -1-ol with a haloformic ester in the presence of a base, and hydrolysis of the compounds (I) under basic conditions gives optically active 3-(N-methylamino)-1-(2-thienyl)-propan-1 -ol: (I) wherein R1 and R2 are each independently alkyl having 1 to 4 carbon atoms, or the like; and * represents an asymmetric center.
PCT/JP2002/008588 2001-08-27 2002-08-26 3-(n-alkoxycarbonyl-n-methyl)amino-1-alkoxycarbonyl- oxy-(2-thienyl)propanes and process for preparing 3-(n- methylamino)-1-(2-thienyl)-propan-1-ol with the same WO2003018572A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001256621A JP2005053781A (en) 2001-08-27 2001-08-27 Method for producing optically active 3-(n-methylamino)-1-(2-thienyl)propan-1-ol
JP2001-256621 2002-05-20

Publications (1)

Publication Number Publication Date
WO2003018572A1 true WO2003018572A1 (en) 2003-03-06

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2002/008588 WO2003018572A1 (en) 2001-08-27 2002-08-26 3-(n-alkoxycarbonyl-n-methyl)amino-1-alkoxycarbonyl- oxy-(2-thienyl)propanes and process for preparing 3-(n- methylamino)-1-(2-thienyl)-propan-1-ol with the same

Country Status (2)

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JP (1) JP2005053781A (en)
WO (1) WO2003018572A1 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003097632A1 (en) * 2002-05-20 2003-11-27 Mitsubishi Rayon Co., Ltd. Propanolamine derivatives, process for preparation of 3-n-methylamino-1-(2-thienyl)-1-propanols and process for preparation of propanolamine derivatives
WO2008004191A2 (en) 2006-07-03 2008-01-10 Ranbaxy Laboratories Limited Process for the preparation of enantiomerically pure salts of n-methyl-3- ( 1-naphthaleneoxy) -3- (2-thienyl) propanamine
CN105061393A (en) * 2015-08-07 2015-11-18 浙江华义医药有限公司 Synthetic method for (S)-(-)-3-methylamino-1-(2-thienyl)-1-propanol
CN109535123A (en) * 2018-12-28 2019-03-29 凯瑞斯德生化(苏州)有限公司 A kind of preparation method of (S) -3- methylamino -1- (2- thienyl) -1- propyl alcohol

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0650965A1 (en) * 1993-10-12 1995-05-03 Eli Lilly And Company Asymmetric synthesis of (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine an intermediate in the preparation of duloxetine

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0650965A1 (en) * 1993-10-12 1995-05-03 Eli Lilly And Company Asymmetric synthesis of (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine an intermediate in the preparation of duloxetine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
LIU H., CHIRALITY, vol. 12, no. 1, 2000, pages 26 - 29, XP009000316 *
WHEELER W.J., J. LABELLED COMP. RADIOPHARM., vol. 36, no. 3, 1995, pages 213 - 223, XP009000253 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003097632A1 (en) * 2002-05-20 2003-11-27 Mitsubishi Rayon Co., Ltd. Propanolamine derivatives, process for preparation of 3-n-methylamino-1-(2-thienyl)-1-propanols and process for preparation of propanolamine derivatives
WO2008004191A2 (en) 2006-07-03 2008-01-10 Ranbaxy Laboratories Limited Process for the preparation of enantiomerically pure salts of n-methyl-3- ( 1-naphthaleneoxy) -3- (2-thienyl) propanamine
CN105061393A (en) * 2015-08-07 2015-11-18 浙江华义医药有限公司 Synthetic method for (S)-(-)-3-methylamino-1-(2-thienyl)-1-propanol
CN109535123A (en) * 2018-12-28 2019-03-29 凯瑞斯德生化(苏州)有限公司 A kind of preparation method of (S) -3- methylamino -1- (2- thienyl) -1- propyl alcohol

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