Sodium borohydride → HCID 54767837, compound

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Reaction Steps

2-Amino-3-[5-(4-phenoxyphenyl)-1H-indol-3-yl]propan-1-ol (10) was prepared as follows: A mixture compound 7 prepared in Example 1 (0.2 g, 1.0 eq) and NaBH4 (4 eq) in 10 mL EtOH was shaken at room temperature for 72 hours. The solvent was removed under vacuum, then, water (10 mL) and EtOAc (40 mL) was added to it. The organic layer was separated, concentrated and purified by column (Silica gel, EtOAc/MeOH 10/1, then EtOAc/MeOH/NH4OH 10/2/0.2) to get compound 10 as a yellow solid (60 mg, 38%): 1H-NMR (400 MHz, CD3OD) δ: 7.76 (s, 1H), 7.6-7.65 (m, 2H), 7.32-7.46 (m, 4H), 7.16 (s, 1H), 7.02-7.12 (m, 5H), 3.74-3.78 (m, 1H), 3.55-3.6 (m, 1H), 3.4-3.46 (m, 1H), 3.06-3.12 (m, 1H), 2.96-3.02 (m, 1H); LC/MS: m/z=359.4 [M+H]+ (Calc: 358.4).

Provenance & Evidence