(S)-tert-butyl 2-(2,2,2-trifluoroacetyl)pyrrolidine-1-carboxylate synthesis

3synthesis methods

Product Name:(S)-tert-butyl 2-(2,2,2-trifluoroacetyl)pyrrolidine-1-carboxylate
CAS Number:913979-70-1
Molecular formula:C11H16F3NO3
Molecular Weight:267.24

913979-68-7 Synthesis

(S)-tert-butyl 2-(2,2,2-trifluoro-1-hydroxyethyl)pyrrolidine-1-carboxylate

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1-Pyrrolidinecarboxylic acid, 2-[2,2,2-trifluoro-1-[(trimethylsilyl)oxy]ethyl]-, 1,1-dimethylethyl ester, (2S)-

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(S)-tert-butyl 2-(2,2,2-trifluoroacetyl)pyrrolidine-1-carboxylate

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Yield:913979-70-1 45%

Reaction Conditions:

with Dess-Martin periodane;trifluoroacetic acid in dichloromethane at 20; for 17 h;

Steps:

130.B

The title compounds from Step A above (721 mg) in dichloromethane (5 ml) were added to Dess Martin periodinane (2.32 g) in dichloromethane (15 ml) with stirring. Trifluoroacetic acid (410 μ) was added drop wise and the turbid reaction mixture stirred for EPO 17 h at rt, after which it was directly coated on silica and purified by column chromatography (silica, cyclohexane/EtOAc 90:10 -> 80:20) to afford the title compound (301 mg, 45 %, [MH-BoC]⁺ = 168).

References:

WO2006/116157,2006,A2 Location in patent:Page/Page column 135-136