Sodium Bicarbonate → HCID 68872593, compound

Participants

Reaction Steps

To a 0° C. solution of 1-[3-(1-tert-butoxycarbonyl-piperidin-4-yl)-propyl]-6-chloro-1H-indole-5-carboxylic acid methyl ester (1.10 g, 2.53 mmol) in toluene (20 mL) was added diisobutylaluminum hydride (1 M in hexanes; 5.06 mL, 5.06 mmol) dropwise. The mixture was stirred for 1 h. Additional diisobutylaluminum hydride (1 M in hexanes; 5.06 mL, 5.06 mmol) was added. After 1 h, the mixture was diluted at rt with satd. aq. NaHCO3 (2 mL), MeOH (5 mL), CHCl3 (10 mL), and satd. aq. sodium potassium tartrate (10 mL). The mixture was stirred vigourously until the layers separated. The organic layer was dried and concentrated to give the crude product (117 mg), which was purified by FCC (EtOAc/hexanes) to give 550 mg (27%) of a white solid. 1H NMR (400 MHz, CDCl3): 7.65 (s, 1H), 7.34 (s, 1H), 7.07 (d, J=3.1, 1H), 6.45 (d, J=3.1, 1H), 4.85-4.80 (m, 2H), 4.04 (t, J=7.1, 2H), 2.69-2.55 (m, 2H), 2.30-2.21 (m, 2H), 1.85-1.76 (m, 2H), 1.62-1.54 (m, 2H), 1.44 (s, 9H), 1.40-1.18 (m, 3H), 1.03 (dq, J=12.6, 4.4, 2H).

Provenance & Evidence