HCID 66936675, compound → methyl N-[(3S)-pyrrolidin-3-yl]carbamate

HRID 1366716Notes

Reaction equation

HRID 1366716 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]1[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7]1)=[O:4]>CO.[Pd]>[NH:8]1[CH2:9][CH2:10][C@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH2:7]1

Participants

4

Reactant 1

HCID 66936675HCID 66936675, compound

Product 1

HCID 58368414methyl N-[(3S)-pyrrolidin-3-yl]carbamateYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Phenylmethyl (3S)-3-{[(methyloxy)carbonyl]amino}-1-pyrrolidinecarboxylate (2.00 g, 7.19 mmol) was dissolved in degassed methanol (20 mL) and Pd/C (0.4 g, 0.376 mmol) was added. The reaction vessel was evacuated and back-filled with hydrogen via a balloon. The reaction was stirred for 2 h after which time the catalyst was removed by filtration through Celite. Evaporation of the solvent yielded methyl (3S)-3-pyrrolidinylcarbamate (0.99 g, 76%) as a clear oil.

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with hydrogen via a balloon
  3. customwas removed by filtration through Celite
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5e6fd5d18e5e46bcb1ed5e50e76a41eb
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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