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

HRID 906934Notes

Reaction equation

HRID 906934 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-79b2ab09fbc2426d9d1f2100c72e9a72
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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