(2S,4S)-N-methanesulfonyl-4-diphenylphosphinyl-2-hydroxymethylpyrrolidine → (2S,4S)-N-methanesulfonyl-4-dicyclohexylphosphinyl-2-hydroxymethylpyrrolidine

HRID 1638408Notes

Reaction equation

HRID 1638408 reaction equation
[CH3:1][S:2]([N:5]1[CH2:9][C@@H:8]([P:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[CH2:7][C@H:6]1[CH2:24][OH:25])(=[O:4])=[O:3].[H][H]>CO>[CH3:1][S:2]([N:5]1[CH2:9][C@@H:8]([P:10]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:7][C@H:6]1[CH2:24][OH:25])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 13665140(2S,4S)-N-methanesulfonyl-4-diphenylphosphinyl-2-hydroxymethylpyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 13665142(2S,4S)-N-methanesulfonyl-4-dicyclohexylphosphinyl-2-hydroxymethylpyrrolidineYield 59,856.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An autoclave was charged with 1.70 g (4.5 m-xol) of (2S,4S)-N-methanesulfonyl-4-diphenylphosphinyl-2-hydroxymethylpyrrolidine [VII], 850 mg of 5% Ph/Al2O3 and 20 ml of methanol, and the mixture was stirred for 2 days at 150° C. under 150 atm. pressure of hydrogen. The reaction mixture was subjected to microfiltration and the filtrate was concentrated and subjected to column chromatography on silica gel (solvent: ethanol) to be separated from a fraction insoluble in the organic solvent. The eluent was concentrated until dryness under reduced pressure whereby 1050 g (yield: 84%) of crystals were obtained.

Workup

  1. concentrationthe filtrate was concentrated
  2. customto be separated from a fraction insoluble in the organic solvent

Sources & evidence

ORD record
ord-dd0577080ad14bc7ac41ca575b653c61
Source dataset
uspto-grants-1989_11
Patent number
US04879389

Reaction notes

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