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

1synthesis methods

Product Name:(S)-tert-butyl 2-(2,2,2-trifluoro-1-hydroxyethyl)pyrrolidine-1-carboxylate
CAS Number:913979-68-7
Molecular formula:C11H18F3NO3
Molecular Weight:269.26

69610-41-9 Synthesis

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81290-20-2 Synthesis

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

913979-68-7
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1-Pyrrolidinecarboxylic acid, 2-[2,2,2-trifluoro-1-[(trimethylsilyl)oxy]ethyl]-, 1,1-dimethylethyl ester, (2S)-

913979-69-8
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Yield:-

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran at 0 - 20; for 1 h;

Steps:

130.A

Commercially available 2-formyl-pyrrolidine-l-carboxylic acid tert-butyl ester (330 mg) in anhydrous THF (5 ml) was cooled to 0 °C and trimethyl-trifluoromethylsilane (300 μ) added, followed by addition of tetrabutylammoniumfluoride (60 μl; 1 M in THF). The reaction mixture was allowed to warm to rt and then stirred for 1 h. After dilution with diethyl ether, the organic phase was washed with brine and the aqueous phase extracted with diethyl ether. The combined organic phases were dried (MgSO₄) and evaporated to afford the title compounds as a 1:1 mixture of alcohol and TMS ether (490 mg, 97 %, [MH-Boc]⁺ = 242 (TMS ether); [MH-Bocf = 170 (alcohol)).

References:

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