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

HRID 906933노트

반응식

HRID 906933 반응식
CON(C)[C:4]([C@@H:6]1[C@@H: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][C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C@@H:6]([CH:4]=[O:5])[CH2:7]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 86627622(3R,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide

생성물 1

HCID 86627623(3R,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carbaldehyde수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (3R,4S)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide 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 dired 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+). compound as a light yellow oil. ES-MS m/e: 393.1 (M+H+).

후처리

  1. customThe reaction was quenched by aq. ammonium chloride solution
  2. extractionextracted with ethylacetate twice
  3. concentrationconcentrated in vaccuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluted by a mixture of heptane and ethyl acetate (3:2)

출처 및 근거

ORD 기록
ord-aeda4308fac946d1800a0882ff0acb8f
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012998B2

반응 노트

불러오는 중…