benzyl (1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-ylcarbamate synthesis

5synthesis methods

Product Name:benzyl (1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-ylcarbamate
CAS Number:877384-16-2
Molecular formula:C19H17F6NO3
Molecular Weight:421.33

871917-79-2 Synthesis

CarbaMic acid, N-[(1S)-2-[3,5-bis(trifluoroMethyl)phenyl]-1-Methyl-2-oxoethyl]-, phenylMethyl ester

871917-79-2
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benzyl (1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxypropan-2-ylcarbamate

877384-16-2
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$288.00/250mg

Yield:877384-16-2 99%

Reaction Conditions:

with aluminum isopropoxide in isopropyl alcohol;toluene at 50; for 15 h;

Steps:

1.2.2-3 [Step 2-3] Preparation of (1 ?,2S)-benzyl-[3,5-bis(trifluoromethyl)phenyl]-1- hydroxypropan-2-yl carbamate

A solution of (S)-benzyl-1-[3,5-bis(trifluoromethyl)phenyl]-1-oxopropan-2-yl carbamate (0.3 g, 0.72 mmol), obtained in step 2-2, in toluene (5.4mL) and isopropyl alcohol (3.6ml_) was added with drops of AI(OPr/)3 (0.22 g, 1.08 mmol) at room temperature, and refluxed at 50 °C for 15 hrs with stirring. The reaction mixture was cooled to room temperature, and the reaction was terminated with 2 N HCI, followed by extraction with ethyl acetate. The organic layer thus formed was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was re-crystallized in hexane, and filtered at a reduced pressure to afford the title compound (0.3 g, 99%). H NMR (400 MHz, CDCI₃) δ 7.75-7.82 (m, 3H), 7.26-7.40 (m, 5H), 5.12 (s, 2H), 5.03 (brs, 1 H), 4.85 (d, J = 7.2 Hz, 1 H), 4.04 (m, 1 H), 3.24 (brs, H), 0.99 (d, J = 7.2 Hz, 3H).

References:

WO2014/157994,2014,A1 Location in patent:Page/Page column 48

1142-20-7 Synthesis