Aluminium lithium hydride → (3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carbaldehyde

HRID 906919ノート

反応式

HRID 906919 の反応式
CON(C)[C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:9][N:8]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:7]1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:19]([N:8]1[CH2:9][CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH:6]([CH:4]=[O:5])[CH2:7]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 86627620(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide

生成物 1

HCID 86627621(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carbaldehyde収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide (3A) 6.58 g (0.017 mol) dissolved in THF (100 mL) was added 16 mL (0.017 mol) of lithiumaluminiumhydride (1.0M in THF) dropwise at 0° C. and stirred for one hour. The reaction was quenched by aq. ammonium chloride solution and extracted with ethylacetate twice. The combined organic layers were dried on anhydrous sodium sulfate and concentrated in vaccuo. The residue was purified by silica gel column chromatography eluted by a mixture of heptane and ethyl acetate (3:2) yielding 5.21 g (93%) of the title compound as a light yellow oil. ES-MS m/e: 334.2 (M+H+).

後処理

  1. customThe reaction was quenched by aq. ammonium chloride solution
  2. extractionextracted with ethylacetate twice
  3. dry with materialThe combined organic layers were dried on anhydrous sodium sulfate
  4. concentrationconcentrated in vaccuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted by a mixture of heptane and ethyl acetate (3:2)

出典と根拠

ORDレコード
ord-5f7db1d47cf84a2c8dc5832847164498
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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