Formic Acid → 1,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

HRID 1780278Notes

Reaction equation

HRID 1780278 reaction equation
C(O)=O.[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C@H:12]1[CH2:24][O:25]CC1C=CC=CC=1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>CO.[Pd]>[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])[C@H:12]1[CH2:24][OH:25])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 57167991HCID 57167991, compound

Product 1

HCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylateYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.4 ml of formic acid were added to a solution of 800 mg (1.90 mmol) of (2R,3S)-1-t-butoxycarbonyl-2-benzyloxymethyl-3-t-butyldimethylsilyloxypyrrolidine [which had been prepared from 1-t-butoxycarbonyl-D-seline benzyl ether in a similar manner to that described by W. R. Ewing et al. in Heterocycles, 27, 2843 (1988)] in 8 ml of methanol, and the mixture was stirred for 3 hours in the presence of 400 mg of palladium black under an atmosphere of hydrogen. At the end of this time, the catalyst was filtered off, and the filtrate was freed from the solvent by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 6:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 620 mg of the title compound as an oil.

Workup

  1. customhad been prepared from 1-t-butoxycarbonyl-D-seline benzyl ether in a similar manner to
  2. filtrationAt the end of this time, the catalyst was filtered off
  3. distillationthe filtrate was freed from the solvent by distillation under reduced pressure
  4. customThe residue was purified by column chromatography through silica gel
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-bcd8164cfd954adfa0c6435f271ae354
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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