Sodium borohydride → HCID 13799992, compound
Reaction equation
[S:1]([N:11]1[C:19]2[C:14](=[C:15]([C:20](=[O:22])[CH3:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[BH4-].[Na+]>CO>[S:1]([N:11]1[C:19]2[C:14](=[C:15]([CH:20]([OH:22])[CH3:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1-(1-tosyl-1H-indol-4-yl)ethanone (500 mg, 1.4 mmol, CASRN 112970-73-7) in dry MeOH (5 mL) at 0° C. was added NaBH4 (80 mg, 2.1 mmol) and the mixture was stirred at RT overnight. The mixture was concentrated in vacuo and the residue was diluted with EtOAc, washed sequentially with water and brine. The organics were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography to afford 420 mg (95%) of 1-(1-tosyl-1H-indol-4-yl)ethanol (282) as white semi-solid: 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=8.4 Hz, 2H), 7.81-7.76 (m, 2H), 7.37 (d, J=8.0 Hz, 2H), 7.31-7.23 (m, 2H), 6.98 (d, J=3.6 Hz, 1H), 5.23 (d, J=4 Hz, 1H), 5.04-5.01 (m, 1H), 2.30 (s, 3H), 1.33 (d, J=6.4 Hz, 3H).