Carbamate → HCID 11647413, compound

Participants

Reaction Conditions

Reaction Steps

4-(3,5-bis(trifluoromethyl)benzyloxy)-3-methyl-3-phenylbutanenitrile (46.2 mg, 0.115 mmol) was treated with neat borane-dimethylsulfide complex for 2 hour at room temperature until completion of reaction. The excess amount of borane was removed under nitrogen stream. The residue was quenched further with methanol and then heated at 80° C. for 1 hour to decompose the borane-amine complex. The resultant solution was concentrated and re-dissolved in CH2Cl2. It was washed with brine and dried with sodium sulfate. After concentration, the residue was mixed with K2CO3 (200 mg) and methyl chloroformate (21.8 mg, 0.23 mmol) in anhydrous CH2Cl2. After stirring overnight, it was worked up routinely and submitted for preparative HPLC. The obtained carbamate was treated with lithium aluminun hydride (0.168 mmol) in THF at 80° C. for 1 hour. Afterwards the reaction mixture was concentrated to dryness under nitrogen stream, re-dissolved in methanol, and purified by preparative HPLC and then silica flash chromatography (10% methanol in CH2Cl2) to give 8.5 mg of the desired product as a free base. 1H NMR (500 MHz, CDCl3) δ ppm 1.42 (s, 3 H) 1.93 (m, 1 H) 2.09 (m, 1 H) 2.35 (s, 3 H) 2.37 (m, 1 H) 2.52 (m, 1 H) 3.54 (s, 2 H) 7.24 (m, 2 H) 7.34 (m, 4 H) 7.65 (s, 2 H) 7.76 (s, 1 H); 13C NMR (500 MHz, CDCl3) δ 144.64, 141.36, 131.68(q, JCCF=33.3 Hz), 128.45, 127.14, 126.65, 126.34, 123.39, (q, JCF=272.5 Hz), 121.4 (m), 80.33, 71.89, 47.16, 41.67, 38.03, 35.70, 22.76.

Provenance & Evidence