Lithium borohydride → [(3RS,4SR)-3-(3,4-dichloro-phenyl)-4-((RS)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-(6-methoxy-pyridin-3-yl)-methanone

HRID 906910노트

반응식

HRID 906910 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([C:14]([C:16]3[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)=[O:15])[CH2:11][CH:10]2[C:24](=[O:26])[CH3:25])[CH:5]=[CH:6][C:7]=1[Cl:8].[Li+].[BH4-]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:10]([CH:24]([OH:26])[CH3:25])[CH2:11][N:12]([C:14]([C:16]3[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)=[O:15])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 671314081-[(3SR,4RS)-4-(3,4-Dichloro-phenyl)-1-(6-methoxy-pyridine-3-carbonyl)-pyrrolidin-3-yl]-ethanone

생성물 1

HCID 67130175[(3RS,4SR)-3-(3,4-dichloro-phenyl)-4-((RS)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-(6-methoxy-pyridin-3-yl)-methanone수율 23.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 1-[(3SR,4RS)-4-(3,4-dichloro-phenyl)-1-(6-methoxy-pyridine-3-carbonyl)-pyrrolidin-3-yl]-ethanone (XIV-1) (0.64 g, 1.60 mmol) in MeOH (10 mL) at −78° C. was added LiBH4 (0.047 g, 1.70 mmol). The temperature was slowly raised to RT (over 1 hour), and the reaction mixture was quenched by addition of H2O. The product was extracted with EtOAc, the combined organic phases were dried over Na2SO4. The two diastereoisomers were separated by column chromatography (SiO2) to yield 0.15 g (23%) of [(3RS,4SR)-3-(3,4-dichloro-phenyl)-4-((RS)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-(6-methoxy-pyridin-3-yl)-methanone (XV-A-1) as a white solid ES-MS m/e: 395.3 (M+H+) and 0.48 g (75%) of [(3RS,4SR)-3-(3,4-dichloro-phenyl)-4-((SR)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-(6-methoxy-pyridin-3-yl)-methanone (XV-B-1) as a white solid ES-MS m/e: 395.3 (M+H+).

후처리

  1. customthe reaction mixture was quenched by addition of H2O
  2. extractionThe product was extracted with EtOAc
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. customThe two diastereoisomers were separated by column chromatography (SiO2)

출처 및 근거

ORD 기록
ord-a2b56f5b7cc54905bdda4f328386ceb1
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012998B2

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