Triethylamine → 3-Butoxycarbonylamino-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1970477Notes

Reaction equation

HRID 1970477 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:24]([O:28][C:29](Cl)=[O:30])[CH2:25][CH2:26][CH3:27]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:29]([O:28][CH2:24][CH2:25][CH2:26][CH3:27])=[O:30])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 2756614Benzyl 3-aminopyrrolidine-1-carboxylate

Product 1

HCID 668544263-Butoxycarbonylamino-pyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.00 g 3-amino-pyrrolidine-1-carboxylic acid benzyl ester hydrotrifluoroacetate in 50 ml dichloromethane were added dropwise 3.7 ml triethylamine and 1.3 ml butylchloroformate at 0° C. After stirring for 12 h the reaction mixture was diluted with dichloromethane, washed with 0.1 M HCl, saturated aqueous NaHCO3 and brine. The crude product thus obtained was purified by flash chromatography on silica using ethyl acetate/heptane 2:3 as eluent. Yield: 648 mg.

Workup

  1. washwashed with 0.1 M HCl, saturated aqueous NaHCO3 and brine

Sources & evidence

ORD record
ord-3ef937b1a3d0458c8306d13417909c83
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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