1-Benzyloxycarbonyl-3-(1-tert-butoxycarbonylaminoethyl)pyrrolidine → tert-butyl N-[1-(pyrrolidin-3-yl)ethyl]carbamate

HRID 2372353Notes

Reaction equation

HRID 2372353 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH:13]([CH:16]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH3:17])[CH2:12]1)=O)C1C=CC=CC=1>[Pd].C(O)C>[C:22]([O:21][C:19]([NH:18][CH:16]([CH:13]1[CH2:14][CH2:15][NH:11][CH2:12]1)[CH3:17])=[O:20])([CH3:23])([CH3:24])[CH3:25]

Participants

4

Reactant 1

HCID 152280501-Benzyloxycarbonyl-3-(1-tert-butoxycarbonylaminoethyl)pyrrolidine

Product 1

HCID 14099015tert-butyl N-[1-(pyrrolidin-3-yl)ethyl]carbamateYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

640 mg of 1-benzyloxycarbonyl-3-(1-tert-butoxycarbonylaminoethyl)pyrrolidine isomer (P-2A) and 300 mg of 5% Pd-C (50% wet) were added to 20 ml of ethanol and catalytic reduction was carried out at room temperature under 3 atm. for 3 h. Then, the catalyst was filtered off and ethanol was distilled off to obtain 390 mg of the desired compound (P-3A) in the form of a colorless, viscous oil.

Workup

  1. filtrationThen, the catalyst was filtered off
  2. distillationethanol was distilled off

Sources & evidence

ORD record
ord-7ed34303c8d34cd69dd4f36f26ccb88e
Source dataset
uspto-grants-1992_03
Patent number
US05098912

Reaction notes

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