Sodium borohydride → HCID 67997514, compound

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Reaction Steps

2-Amino-3-[1-(4-phenoxyphenyl)-1H-indol-3-yl]propan-1-ol (34) was prepared as follows: A mixture of compound 33 (0.15 g, 1.0 eq) and NaBH4 (4 eq) in 15 mL of EtOH was shaken at room temperature for 72 hours. The solvent was removed under vacuum. Water (10 mL) and EtOAc (40 mL) were added to the residue. The organic layer was separated, concentrated and purified by column (Silica gel, EtOAc/MeOH/NH4OH 10/2/0.2) to get a sticky oil, which was dissolved in 25 mL of HCl (0.25N aqueous), then, freeze dried to afford compound 34 as a brown solid (45 mg, 35%): 1H-NMR (400 MHz, CD3OD) δ: 7.59 (d, 1H, 7.9 Hz), 7.4-7.44 (m, 3H), 7.28-7.32 (m, 3H), 7.04-7.15 (m, 5H), 6.95-6.99 (m, 2H), 3.7-3.74 (m, 1H), 3.47-3.58 (m, 2H), 3.01-3.12 (m, 2H); LC/MS: m/z=359.1 [M+H]+ (Calc: 358.4).

Provenance & Evidence