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

HRID 906934ノート

反応式

HRID 906934 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-79b2ab09fbc2426d9d1f2100c72e9a72
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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