3-[(4-Chloro-benzyl)-methoxycarbonylmethyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester → [(4-Chloro-benzyl)-pyrrolidin-3-yl-amino]-acetic acid methyl ester

HRID 1983740Notes

Reaction equation

HRID 1983740 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[CH3:18][O:17][C:15](=[O:16])[CH2:14][N:13]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)[CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

4

Reactant 1

HCID 667583843-[(4-Chloro-benzyl)-methoxycarbonylmethyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66758681[(4-Chloro-benzyl)-pyrrolidin-3-yl-amino]-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

3-[(4-Chloro-benzyl)-methoxycarbonylmethyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (3.5 g, 9.1 mmol) was dissolved in 4N HCl in dioxane (60 mL). The resultant solution was stirred for 2 h at rt then concentrated to provide the desired product as a white solid. LCMS (retention time=1.26, ES+283)

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-4b110f64416049ca8a7b5bc2d8f2a0e3
Source dataset
uspto-grants-2009_06
Patent number
US07541365B2

Reaction notes

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