(2S,4R)-1-benzyloxycarbonyl-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidine → (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidine

HRID 703592Notes

Reaction equation

HRID 703592 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH2:24][OH:25])=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:25][CH2:24][CH2:23][O:22][CH2:21][C@@H:12]1[CH2:13][C@@H:14]([O:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH2:15][NH:11]1

Participants

5

Reactant 2

HCID 18642542(2S,4R)-1-benzyloxycarbonyl-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 57005235(2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (2S,4R)-1-benzyloxycarbonyl-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidine (53.0 g) in methanol (530 ml) was hydrogenated under atmospheric pressure of hydrogen at ambient temperature for 4 hours in the presence of 10% palladium on carbon (5.3 g, 50% wet). The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (200 g) and eluted with a mixture of methanol and dichloromethane (5:95 V/V) to give (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidine (30.55 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a syrup
  4. washeluted with a mixture of methanol and dichloromethane (5:95 V/V)

Sources & evidence

ORD record
ord-f2acdf7e640c48fdb210c1a81be86209
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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