Lithium Hydroxide → 4-[2-Carboxy-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-1-yl]-piperidine-1-carboxylic Acid Tert-butyl Ester

HRID 1697646Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH:17]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([F:31])([F:30])[F:29])(=[O:21])=[O:20])[CH2:16][CH:15]2[C:32]([O:34]CC)=[O:33])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:18][CH:17]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([F:29])([F:30])[F:31])(=[O:21])=[O:20])[CH2:16][CH:15]2[C:32]([OH:34])=[O:33])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 667708904-[2-Ethoxycarbonyl-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-1-yl]-piperidine-1-carboxylic Acid Tert-butyl Ester

Product 1

HCID 667710184-[2-Carboxy-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-1-yl]-piperidine-1-carboxylic Acid Tert-butyl Ester

Procedure

In analogy to the procedure described in example 253e, 4-[2-ethoxycarbonyl-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was saponified in the presence of lithium hydroxide to give the title compound as off-white solid which was used in the next step without further purification. MS (ESI): m/z=507.3 [M+H]+.

Sources & evidence

ORD record: ord-e6c61fdd9cad4f9e97f6da66790f2368
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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