Diisopropylethylamine → 1-Boc-3-aminopyrrolidine

HRID 352757Notes

Reaction equation

HRID 352757 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-fb91d25279264384bea7f8a0bf9ade5c
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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