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

HRID 906928ノート

反応式

HRID 906928 の反応式
[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:24])[CH2:22][CH3:23])[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:24])[CH2:22][CH3:23])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 671316011-[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-one

生成物 1

HCID 67131651(RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-one (211 mg, 0.5825 mmol) in THF (5 mL) was added LAH (1M in THF, 0.58 mL, 0.58 mmol) at 0° C. and stirred for 30 minutes. The reaction was quenched by an addition of aq. KF solution (135 mg in 0.5 mL of water). The mixture was stirred vigorously for 10 minutes followed by an addition of anhydrous sodium sulfate. The insoluves were removed by filtration through a cotton pad and the cake was washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (heptane/ethyl acetate 3:1 to 1:1) yielding (RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-ol as a light yellow oil with ES-MS m/e: 364.1 (M'H+) and (SR)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-ol as a light yellow oil. ES-MS m/e: 364.1 (M+H+).

後処理

  1. customThe reaction was quenched by an addition of aq. KF solution (135 mg in 0.5 mL of water)
  2. stirringThe mixture was stirred vigorously for 10 minutes
  3. additionfollowed by an addition of anhydrous sodium sulfate
  4. customThe insoluves were removed by filtration through a cotton pad
  5. washthe cake was washed with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate 3:1 to 1:1)

出典と根拠

ORDレコード
ord-0d16b97b67714005bfab85feca66e95d
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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