Triethylamine → 3-Benzyloxycarbonylamino-pyrrolidine-1-carboxylic acid butyl ester

HRID 1970472Notes

Reaction equation

HRID 1970472 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[NH:10][CH:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)[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>[CH2:24]([O:28][C:29]([N:13]1[CH2:14][CH2:15][CH:11]([NH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:16])[CH2:12]1)=[O:30])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 112067813-N-Cbz-aminopyrrolidine

Product 1

HCID 668545503-Benzyloxycarbonylamino-pyrrolidine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.20 g pyrrolidin-3-yl-carbamic acid benzyl ester hydrotrifluoracetate in 50 ml dichloromethane were added dropwise 3.7 ml triethylamine and 1.3 ml butylchloro-formate at 0° C. After stirring for 12 h the reaction mixture was diluted with dichloromethane, washed with 0.1 M HCl, saturated NaHCO3 and brine. The crude product thus obtained was purified by flash chromatography on silica using ethyl acetate/heptane 1:2 as eluent.

Workup

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

Sources & evidence

ORD record
ord-a792b96296cc409bb0ae95a7f4acde23
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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