Acetic acid, 2-chloro-, phenylmethyl ester → HCID 67506082, compound

HRID 2384104Notes

Reaction equation

HRID 2384104 reaction equation
[CH2:1]([O:8][C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:14][O:15][C:16]([C@@H:18]1[CH2:22][CH2:21][CH2:20][NH:19]1)=[O:17].C(N(C(C)C)CC)(C)C>C(Cl)Cl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:14][O:15][C:16]([C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:12])=[O:17]

Participants

6

Reactant 3

HCID 8786Acetic acid, 2-chloro-, phenylmethyl esterHCID 81531DiisopropylethylamineHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 67506082HCID 67506082, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of chloroacetic benzyl ester (1.8 g, 9.75 mmol) in DCM (50 mL) is added (S)-pyrrolidine-2-carboxylic acid methyl ester hydrochloride (1.51 g, 11.70 mmol), diisopropylethylamine (4.09 mL, 23.40 mmol) and tetrabutylammonium iodide (3.60 g, 9.75 mmol) and the resulting mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure and the residue purified by column chromatography using a gradient of 2-45% EtOAc/heptane to give (S)-1-benzyloxycarbonylmethyl-pyrrolidine-2-carboxylic acid methyl ester; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.81-2.05 (m, 3H), 2.13-2.24 (m, 1H), 2.78-2.84 (m, 1H), 3.15-3.20 (m, 1H), 3.57-3.69 (m, 3H), 3.70 (s, 3H), 5.15 (s, 2H), 7.36 (m, 5H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-984dce84f7114317a7df8d4139857fab
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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