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

HRID 906910ノート

反応式

HRID 906910 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-a2b56f5b7cc54905bdda4f328386ceb1
出典データセット
uspto-grants-2011_09
特許番号
US08012998B2

反応ノート

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