2-Butyl-2-[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-benzoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester → (4-Amino-3-chloro-phenyl)-(2-butyl-pyrrolidin-2-yl)-methanone

HRID 661544Notes

Reaction equation

HRID 661544 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:31][CH2:32][CH2:33][CH3:34])[C:13](=[O:30])[C:14]1[CH:19]=[CH:18][C:17]([N:20]([Si](C)(C)C)[Si](C)(C)C)=[C:16]([Cl:29])[CH:15]=1)=O)(C)(C)C>Cl>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([C:9]2([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:30])=[CH:15][C:16]=1[Cl:29]

Participants

3

Reactant 1

HCID 666875712-Butyl-2-[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-benzoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58017243(4-Amino-3-chloro-phenyl)-(2-butyl-pyrrolidin-2-yl)-methanoneYield 226.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-butyl-2-[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-benzoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.205 g, 0.391 mmol) in methanolic 1N HCl (7.8 mL) was stirred at 50° C. under nitrogen for 2 hours. The reaction mixture was concentrated in vacuo to yield (4-amino-3-chloro-phenyl)-(2-butyl-pyrrolidin-2-yl)-methanone (0.249 g, quantitative yield) as a light brown powder and as a monohydrochloride salt.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-a3d9a0daa1be4c479338268de8d15774
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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