KR970042499A - Method for preparing 4- (N-t-butoxycarbonyl) aminomethyl-1- (N-t-butoxycarbonyl) pyrrolidin-3-ol - Google Patents

Method for preparing 4- (N-t-butoxycarbonyl) aminomethyl-1- (N-t-butoxycarbonyl) pyrrolidin-3-ol Download PDF

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KR970042499A
KR970042499A KR1019950058701A KR19950058701A KR970042499A KR 970042499 A KR970042499 A KR 970042499A KR 1019950058701 A KR1019950058701 A KR 1019950058701A KR 19950058701 A KR19950058701 A KR 19950058701A KR 970042499 A KR970042499 A KR 970042499A
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KR
South Korea
Prior art keywords
sodium borohydride
butoxycarbonyl
formula
mixture
trifluoroacetic acid
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KR1019950058701A
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Korean (ko)
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KR0156621B1 (en
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김세호
최훈
장재혁
남두현
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성재갑
주식회사 엘지화학
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Priority to KR1019950058701A priority Critical patent/KR0156621B1/en
Publication of KR970042499A publication Critical patent/KR970042499A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 구조식 (1)의 화합물을 나트륨보로하이드라이드, 나트륨보로하이드라이드와 트리플루오로아세트산의 혼합물 및 무수 t-부틸옥시카르보닐산과 순차적으로 반응시킴을 특징으로하여 1단계 공정에 의해 퀴놀론계 항생제의 제조시에 중간체로 유용한 구조식 (2)의 4-(N-t-부톡시카르보닐)아미노메틸-1-(N-t-부톡시카르보닐)피롤리딘-3-올을 경제적으로 간편하게 제조하는 효율적인 방법에 관한 것이다.The present invention is characterized in that the compound of formula (1) is sequentially reacted with sodium borohydride, a mixture of sodium borohydride and trifluoroacetic acid and t-butyloxycarbonyl anhydride in a one-step process. Economical and convenient preparation of 4- (Nt-butoxycarbonyl) aminomethyl-1- (Nt-butoxycarbonyl) pyrrolidin-3-ol of formula (2), useful as an intermediate in the preparation of quinolone antibiotics An efficient way to do this.

상기식에서, tBoc는 t-부틸옥시카르보닐기를 의미한다.In the above formula, tBoc means t-butyloxycarbonyl group.

Description

4-(N-t-부톡시카르보닐)아미노메틸-1-(N-t-부톡시카르보닐)피롤리딘-3-올의 제조방법Method for preparing 4- (N-t-butoxycarbonyl) aminomethyl-1- (N-t-butoxycarbonyl) pyrrolidin-3-ol

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (9)

구조식 (1)의 화합물을 나트륨보로하이드라이드, 나트륨보로하이드라이드와 트리플루오로아세트산의 혼합물 및 무수 t-부틸옥시카르보닐산과 순차적으로 반응시킴을 특징으로하여 구조식 (2)의 4-(N-t-부톡시카르보닐)아미노메틸-1-(N-t-부톡시카르보닐)피롤리딘-3-올을 제조하는 방법.The compound of formula (1) is reacted sequentially with sodium borohydride, a mixture of sodium borohydride and trifluoroacetic acid, and t-butyloxycarbonyl anhydride, so that 4- ( A process for preparing Nt-butoxycarbonyl) aminomethyl-1- (Nt-butoxycarbonyl) pyrrolidin-3-ol. 상기식에서, tBoc 는 t-부틸옥시카르보닐기를 의미한다.In the formula, tBoc means t-butyloxycarbonyl group. 제1항에 있어서, 나트륨보로하이드라이드, 나트륨보로하이드라이드와 트리플루오로아세트산의 혼합물의 각 성분, 및 무수 t-부틸옥시카르보닐산을 구조식 (1)의 화합물에 대하여 동몰량 내지 과량으로 사용함을 특징으로 하는 방법.The method according to claim 1, wherein each component of sodium borohydride, a mixture of sodium borohydride and trifluoroacetic acid, and t-butyloxycarbonyl anhydride are equimolar to an excess with respect to the compound of formula (1). Characterized in that used as. 제2항에 있어서, 구조식 (1)의 화합물에 대하여 나트륨보로하이드라이드를 동몰량으로 사용하고, 나트륨보로하이드라이드와 트리플루오로아세트산의 혼합물의 각 성분은 동몰량 내지 2배 몰량으로 사용하며, 무수 t-부틸옥시카르보닐산은 동몰량으로 사용함을 특징으로 하는 방법.The method of claim 2, wherein sodium borohydride is used in an equimolar amount relative to the compound of formula (1), and each component of the mixture of sodium borohydride and trifluoroacetic acid is used in an equimolar amount to 2 times molar amount. And t-butyloxycarbonyl anhydride is used in equimolar amounts. 제1항에 있어서, 나트륨보로하이드라이드와 트리플루오로아세트산의 혼합물을 반응용액의 내부온도를 20℃ 이하로 유지시키면서 첨가함을 특징으로 하는 방법.The method of claim 1, wherein a mixture of sodium borohydride and trifluoroacetic acid is added while maintaining the internal temperature of the reaction solution at 20 ° C or lower. 제1항에 있어서, 무수 t-부틸옥시카르보닐산을 첨가하기 전에 물을 첨가함을 특징으로 하는 방법.The method according to claim 1, wherein water is added before adding t-butyloxycarbonyl anhydride. 제5항에 있어서, 물의 첨가시에 반응용액의 내부온도를 0 내지 5℃로 유지시킴을 특징으로 하는 방법.The method according to claim 5, wherein the internal temperature of the reaction solution is maintained at 0 to 5 DEG C upon addition of water.
KR1019950058701A 1995-12-27 1995-12-27 Process for preparation of 4-(n-t-butloxycarbonyl)aminomethyl-1-(n-t-butyloxycarbonyl)pyrrolidin-3-ol KR0156621B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019950058701A KR0156621B1 (en) 1995-12-27 1995-12-27 Process for preparation of 4-(n-t-butloxycarbonyl)aminomethyl-1-(n-t-butyloxycarbonyl)pyrrolidin-3-ol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019950058701A KR0156621B1 (en) 1995-12-27 1995-12-27 Process for preparation of 4-(n-t-butloxycarbonyl)aminomethyl-1-(n-t-butyloxycarbonyl)pyrrolidin-3-ol

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KR970042499A true KR970042499A (en) 1997-07-24
KR0156621B1 KR0156621B1 (en) 1998-11-16

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