Methyltriphenylphosphonium iodide → (3S,4R)-1-Benzyl-3-(3,4-dichloro-phenyl)-4-vinyl-pyrrolidine

HRID 906934노트

반응식

HRID 906934 반응식
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li]CCCC.[CH2:27]([N:34]1[CH2:38][C@H:37]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([Cl:46])[CH:40]=2)[C@@H:36]([CH:47]=O)[CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[CH2:27]([N:34]1[CH2:35][C@H:36]([CH:47]=[CH2:2])[C@@H:37]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([Cl:46])[CH:40]=2)[CH2:38]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 3

HCID 638159Methyltriphenylphosphonium iodideHCID 86627623(3R,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carbaldehydeHCID 178418339Butyllithium

생성물 1

HCID 67131470(3S,4R)-1-Benzyl-3-(3,4-dichloro-phenyl)-4-vinyl-pyrrolidine수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of methyltriphenylphosphonium iodide (5.53 g, 0.0136 mol) in THF (50 mL) was added n-BuLi (1.6N in heptane, 6.5 mL, 0.0104 mol) dropwise at 0° C. and stirred for one hour. To this reaction mixture was added a solution of (3R,4S)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carbaldehyde 2.68 g (0.008 mol) in THF (15 mL) dropwise at 0° C. and stirred for another one hour. The reaction was quenched by aq. ammonium chloride solution and extracted with ethylacetate. The separated organic layer was 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 (4:1) yielding 2.12 g (80%) of the title compound as a light yellow oil. ES-MS m/e: 332.1 (M+H+).

후처리

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

출처 및 근거

ORD 기록
ord-79b2ab09fbc2426d9d1f2100c72e9a72
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012998B2

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