Diisopropylethylamine → 1-Boc-3-aminopyrrolidine

HRID 1061046Notes

Reaction equation

HRID 1061046 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[C:16]([O:20][C:21](ON=C(C1C=CC=CC=1)C#N)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CO>[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 1644013-Aminopyrrolidine

Product 1

HCID 27563701-Boc-3-aminopyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (30 ml), 3-aminopyrrolidine (0.54 g) was dissolved under ice cooling, followed by the addition of diisopropylethylamine (720 μl) and 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (0.84 g). The resulting mixture was gradually heated to room temperature and stirred for 11 hours. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (dichloromethane˜5% methanol-dichloromethane), whereby the title compound (0.59 g, 94%) was obtained.

Workup

  1. customThe residue obtained
  2. distillationby distilling off the solvent under reduced pressure
  3. customwas purified by chromatography on a silica gel column (dichloromethane˜5% methanol-dichloromethane), whereby the title compound (0.59 g, 94%)
  4. customwas obtained

Sources & evidence

ORD record
ord-79ea9dcb802e48cb8a6ecfe8a9b7a9ee
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

Loading…