3-(t-Butoxycarbonylamino)-1-benzyl-4-methylpyrrolidine → tert-Butyl (4-methylpyrrolidin-3-yl)carbamate

HRID 1722291Notes

Reaction equation

HRID 1722291 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH:13]([CH3:14])[CH2:12][N:11](CC2C=CC=CC=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH:13]([CH3:14])[CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 139331343-(t-Butoxycarbonylamino)-1-benzyl-4-methylpyrrolidine

Product 1

HCID 14738853tert-Butyl (4-methylpyrrolidin-3-yl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 3-(t-butoxycarbonylamino)-1-benzyl-4-methylpyrrolidine (3.9 g) are added ethanol (50 ml) and 10% Pd-C (780 mg), and the mixture is subjected to catalytic reduction at 60° C. under atmospheric pressure. After the catalytic reduction, the catalyst is removed off by filtration, and the filtrate is concentrated. The resulting residue is recrystallized from ethyl acetate-petroleum ether to give 3-(t-butoxycarbonylamino)-4-methylpyrrolidine (isomer A) (2.01 g), as colorless prisms, m.p. 86.8°-87° C.

Workup

  1. customis subjected to catalytic reduction at 60° C. under atmospheric pressure
  2. customAfter the catalytic reduction, the catalyst is removed off by filtration
  3. concentrationthe filtrate is concentrated
  4. customThe resulting residue is recrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-3e534069584045d5b59ca9e29c8527b0
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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