Potassium Carbonate → 3-(Carbamoylmethyl-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 457197Notes

Reaction equation

HRID 457197 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.Br[CH2:15][C:16]([NH2:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][CH:2]([NH:1][CH2:15][C:16](=[O:17])[NH2:18])[CH2:3]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Product 1

HCID 667584463-(Carbamoylmethyl-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-3-amino-1-N-Boc pyrrolidine (0.5 g, 2.68 mmol) and 2-bromo acetamide (0.44 g, 3.21 mmol) in DMF (6.0 mL) was added potassium carbonate (1.11 g, 8.04 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and re-dissolved in dichloromethane. Potassium carbonate was filtered off and filtrate was concentrated and purified using ethyl acetate/methanol (5%). 1H-NMR (CDCl3) δ: 1.50 (9H, s), 1.60–1.80 (2H, m), 2.10 (1H, m), 3.10–3.60 (6H, m), 5.65 (1H, br, s), 6.90 (1H, br, s). ESI-MS m/z: 367(M+1), UV retention time: 0.61 min.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionre-dissolved in dichloromethane
  3. filtrationPotassium carbonate was filtered off
  4. concentrationfiltrate was concentrated
  5. custompurified

Sources & evidence

ORD record
ord-7c16cbb56168420991abcfbd4633ed4a
Source dataset
uspto-grants-2007_03
Patent number
US07186729B2

Reaction notes

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