Benzyl (3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate → (3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

HRID 2073176Notes

Reaction equation

HRID 2073176 reaction equation
[CH3:1][C:2]([CH3:23])([O:4][C:5]([NH:7][C@H:8]1[CH2:12][CH2:11][N:10](C(OCC2C=CC=CC=2)=O)[CH2:9]1)=[O:6])[CH3:3].[H][H]>CO.[Pd]>[CH3:3][C:2]([CH3:23])([O:4][C:5]([NH:7][C@H:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)=[O:6])[CH3:1]

Participants

5

Reactant 2

HCID 14555479Benzyl (3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 17.7 g (55.2 mmol) of (S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinecarboxylic acid, phenylmethyl ester, in 400 ml of methanol was treated with 2.0 g of 20% palladium on carbon and shaken in an atmosphere of hydrogen at temperatures of 22°-26.5° and pressures of 45-50.5 psi for one hour. The solvent was removed in vacuo to give 10.1 g of the title compound.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5ac8305e4a414aafb28a0ac21f358b58
Source dataset
uspto-grants-1990_04
Patent number
US04916141

Reaction notes

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