tert-Butanol → N-[4-(2-carbamoylethyl)cyclohexyl]-N-cyclopropyl-4-[(2S)-1,1,1-trifluoro-2-hydroxypropan-2-yl]benzamide

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Reaction Conditions

Reaction Steps

To (S)—N-(4-(2-cyanoethyl)cyclohexyl)-N-cyclopropyl-4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzamide prepared above (0.040 g, 0.098 mmol) and KOH (0.55 g, 0.98 mmol) was added tert-butanol (3.75 mL). The mixture was heated to 85° C. and stirred for 15 h. The solution was diluted with water (10 mL) and extracted with 10% MeOH in CH2Cl2 (2×15 mL). The combined organics were dried over Na2SO4 and removed in vacuo. Silica gel chromatography (gradient of 0-10% MeOH in CH2Cl2) afforded (S)—N-(4-(3-amino-3-oxopropyl)cyclohexyl)-N-cyclopropyl-4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzamide. 1H NMR (500 MHz, CD3OD): δ 0.45 (bs, 2H), 0.58 (bs, 2H), 1.05-1.15 (m, 2H), 1.27-1.48 (m, 2H), 1.51-1.59 (m, 2H), 1.77 (s, 3H), 1.90-2.00 (m, 5H), 2.25-2.28 (m, 2H), 2.71 (bs, 1H), 4.00 (bs, 1H), 7.52 (d, J=8 Hz, 2H), 7.70 (d, J=8 Hz, 2H).

Provenance & Evidence