Trifluoroacetic acid → HCID 68778166, compound

HRID 1177030Notes

Reaction equation

C(OC([N:8]1[CH2:12][C:11]([F:14])([F:13])[CH2:10][CH:9]1[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])=O)(C)(C)C.[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24]>ClCCl>[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24].[CH2:18]([O:17][C:15]([CH:9]1[CH2:10][C:11]([F:14])([F:13])[CH2:12][NH:8]1)=[O:16])[CH:19]=[CH2:20]

Participants

Conditions

Temperature: 25 °C

Procedure

4,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-tert-butyl ester (Example 14c, 5.85 g, 20.09 mmol) was dissolved in a 5% solution of trifluoroacetic acid in dichloromethane and stirred at 25° C. for 16 h. The solvent was removed in vacuo and the crude 4,4-difluoro-pyrrolidine-2-carboxylic acid allyl ester (6.14 g, 20.09 mmol, 100% yield) was obtained as the trifluoroacetic acid salt, which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ: 2.75-2.86 (1H, m), 2.90-3.02 (1H, m), 3.76-3.93 (2H, m), 4.68-4.78 (3H, m), 5.33-5.39 (2H, m), 5.84-5.94 (1H, m).

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-a2b5c6a093254040a10eaee6861d8b58
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842838B2

Reaction notes

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