Methanol → methyl (2S,4R)-4-(tert-butyl(dimethyl)silyl)oxy-1-methyl-pyrrolidine-2-carboxylate

HRID 34096Notes

Reaction equation

HRID 34096 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:7][NH:6]1)=[O:4].[H][H].[CH3:20]O>C=O.[Pd]>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:7][N:6]1[CH3:20])=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 15758873methyl (2S,4R)-4-[(tert-butyldimethylsilyl)oxy]pyrrolidine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 60034901methyl (2S,4R)-4-(tert-butyl(dimethyl)silyl)oxy-1-methyl-pyrrolidine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 712FormaldehydeSolvent

Procedure

To a solution of 800 mg of (2S, 4R)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-2-carboxylic acid methyl ester in 8 mL of methanol, 0.35 mL of 37% formalin and 80 mg of 10% palladium on carbon were added, and stirred at 4 atm. Hydrogen pressure for 10 hours. After filtering out the catalyst, the solvent was evaporated, and the residue was separated and purified by silica gel column chromatography (ethyl acetate:n-hexane=1:6), to afford 489 mg of the title compound as a colorless oil.

Workup

  1. filtrationAfter filtering out the catalyst
  2. customthe solvent was evaporated
  3. customthe residue was separated
  4. custompurified by silica gel column chromatography (ethyl acetate:n-hexane=1:6)

Sources & evidence

ORD record
ord-3c7c2b95b148431784c959aaa7702b78
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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