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

HRID 906943Notes

Reaction equation

HRID 906943 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]([F:45])=[C:41]([F: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]([F:45])=[C:41]([F: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 86627625(3R,4S)-1-Benzyl-4-(3,4-difluoro-phenyl)-pyrrolidine-3-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 67131495(3S,4R)-1-Benzyl-3-(3,4-difluoro-phenyl)-4-vinyl-pyrrolidineYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of methyltriphenylphosphonium iodide (6.35 g, 15.6 mmol) in THF (60 mL) was added n-BuLi (1.6N in heptane, 7.4 mL, 0.0119 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-difluoro-phenyl)-pyrrolidine-3-carbaldehyde 2.77 g (9.2 mmol) 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 (7:3) yielding 1.7 g (62%) of the title compound as a light yellow oil ES-MS m/e: 300.1 (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 (7:3)

Sources & evidence

ORD record
ord-17990f086b9a4bd7b462ddb99a84c0da
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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