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848192-92-7

1-Benzhydryl-3-(trifluoroMethyl)azetidin-3-ol synthesis

1synthesis methods
40320-60-3 Synthesis
1-BENZHYDRYLAZETIDIN-3-ONE

40320-60-3
231 suppliers
$6.00/1g

81290-20-2 Synthesis
(Trifluoromethyl)trimethylsilane

81290-20-2
420 suppliers
$13.00/1g

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Yield:848192-92-7 76%

Reaction Conditions:

Stage #1: N-benzhydryl 3-azetidinone;(trifluoromethyl)trimethylsilanewith cesium fluoride in tetrahydrofuran at 23; for 0.25 h;
Stage #2: with tetrabutyl ammonium fluoride;water;ammonium chloride in tetrahydrofuran; for 24 h;

Steps:

A-4

To a solution of L-BENZHYDRYL-AZETIDIN-3-ONE (A) (2. 00G, 8.43 mmol) in 7 mL tetrahydrofuran at 23 °C was added trifluoromethyltrimethylsilane (1.80g, 12.6 mmol) followed by cesium fluoride (1.95g, 12.8 mmol). After 15 minutes, the reaction was quenched by the addition of 7 mL of saturated aqueous ammonium chloride and 1.00 g of tetrabutylammonium fluoride hydrate. The resulting biphasic mixture was stirred vigorously for 1 day then extracted with diethyl ether (3 times). The combined organic layers were dried over sodium sulfate and evaporation in vacuo gave an orange oil that was purified by silica gel chromatography (gradient 2% to 10% isopropanol in dichloromethane) to give 1.98g (76%) of the title compound. MS (APCI+): 308.1 (M+1/Z) ; 349.1 (m+41/z) (acetonitrile)

References:

WO2005/26146,2005,A1 Location in patent:Page 46