Potassium Carbonate → 3-(4-Chloro-benzylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 917205Notes

Reaction equation

HRID 917205 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.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][CH:2]([NH:1][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([Cl:14])=[CH:16][CH:17]=2)[CH2:3]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Product 1

HCID 667576703-(4-Chloro-benzylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-3-amino-1-N-Boc pyrrolidine (1.0 eq, 2.68 mmol), 4-chlorobenzyl bromide (1.0 eq, 2.68 mmol), and potassium carbonate (1.75 eq) were mixed in ethanol (10 mL) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, taken up in ethyl acetate, filtered and concentrated. The crude product was purified by flash chromatography on silica using ethyl acetate. ESI-MS m/z: 311 (M+1), WV retention time: 1.18 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-ba696f9ccbc64e40ade317f35166699a
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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