Methanol → HCID 20672303, compound

Participants

Reaction Steps

A solution of 156 mg (0.36 mmol) of (3-(1-t-butoxycarbonyl-piperidin-4-yl)-2-(R)methylpropyl)-4-(S)-benzyloxazolidin-2-one (from EXAMPLE 99, Step A) in 3 mL of THF at O° C. was treated with 0.03 mL (0.73 mmol) of MeOH followed by 16 mg (0.73 mmol) of lithium borohydride. The cooling bath was removed, the mixture was warmed to rt and stirred for 3 h. The reaction was quenched with H2O and sat'd sodium potassium tartrate. The quenched mixture was diluted with CH2Cl2 and stirred for 1 h, then extracted 3× with CH2Cl2. The combined organic layers were washed with sat'd NaCl, dried over Na2SO4, filtered and the filtrate concentrated. Purification by silica gel column chomatography with 0-25% EtOAc/hexanes (v/v) provided 72 mg (77%) of the title compound: 1H NMR (500 MHz) δ 0.92 (d, J=6.8,33H). 1.01-1.12 (3H), 1.27-1.33 (m, 1H), 1.45 (s, 9H), 1.46-1.50 (m, 1H), 1.61-1.75 (4H), 2.69 (bq, 2H), 3.41 (dd, J=3.9,6.6 Hz, 1H). 3.49 (dd, J=4.8, 5.7, 1H). 4.07 (bd, 2H).

Provenance & Evidence