Ammonia → HCID 54440118, compound

HRID 620793Notes

Reaction equation

HRID 620793 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][O:22][CH2:23][C:24]([O:26]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:28]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][O:22][CH2:23][C:24](=[O:26])[NH2:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54327365HCID 54327365, compound

Product 1

HCID 54440118HCID 54440118, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2S,4R)-1-t-butoxycarbonyl-4-t-butyl dimethylsilyloxy-2-(methoxycarbonylmethyloxymethyl)pyrrolidine (0.75 g) in methanol (21 ml) was saturated with ammonia at ambient temperature and the solution was stirred at the same temperature for 5 hours. The mixture was concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (15 g) and eluted with a mixture of methanol and chloroform (1:99 V/V) to give (2S,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-(carbamoylmethyloxymethyl)pyrrolidine (0.61 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a syrup
  3. washeluted with a mixture of methanol and chloroform (1:99 V/V)

Sources & evidence

ORD record
ord-dc1e553f968645118ac2961be0d1fee5
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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