Aluminium lithium hydride → (RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanol

HRID 1158645노트

반응식

HRID 1158645 반응식
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH:10]([C:21](=[O:23])[CH3:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH:10]([CH:21]([OH:23])[CH3:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 669997301-[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanone

생성물 1

HCID 66999712(RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanol수율 31.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-[(3SR,4RS) 1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanone (IX-1) (14.90 g, 0.043 mol) in THF (300 mL) at 0° C. were added portionwise LiAlH4 (2.05 g 0.051 mol). Stirring was continued for one hour, and the reaction mixture was carefully quenched by addition of aq. NH4Cl, concentrated under vacuo and the product extracted with EtOAC. The combined organic phases were dried on Na2SO4 and concentrated under vacuo. The two diastereoisomeres were separated by column chromatography (SiO2, EtOAc/H, 1:1) to yield (SR)-1-[(3SR,4RS)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanol (XIII-B-1) 4.69 g (31%) as a white solid ES-MS m/e: 350.2 (M+H+) and (RS)-1-[(3SR,4RS)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanol (XIII-A-1) 5.30 g (35%) as a white solid ES-MS m/e: 350.2 (M+H+).

후처리

  1. customthe reaction mixture was carefully quenched by addition of aq. NH4Cl
  2. concentrationconcentrated under vacuo
  3. extractionthe product extracted with EtOAC
  4. customThe combined organic phases were dried on Na2SO4
  5. concentrationconcentrated under vacuo
  6. customThe two diastereoisomeres were separated by column chromatography (SiO2, EtOAc/H, 1:1)

출처 및 근거

ORD 기록
ord-51c14cdc6a324aaa94cb9d888a65c610
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812021B2

반응 노트

불러오는 중…