Water → HCID 14950483, compound

Participants

Reaction Conditions

Reaction Steps

Lithium borohydride (66 mg) was added over a period of 10 minutes to a solution of compound A (800 mg) in tetrahydrofuran (THF) (25 ml) stirred at 0° C. under an atmosphere of argon. The solution was then stirred at ambient temperature for 16 hours, cooled to 0° C. and water (100 ml) was added. The mixture was extracted with dichloromethane (2×50 ml) and the extracts were washed with saturated sodium chloride solution (50 ml) and dried (MgSO4). The solvent was removed by evaporation and the residue purified by flash chromatography, eluting with methanol/dichloromethane (1:19 v/v, to give 3-hydroxymethyl-2,6-dimethyl-4-[(2'-(2-triphenylmethyl-2-H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine (B) (246 mg), as a foam; NMR (d6 -DMSO/d4 -acetic acid): 2.55(s,3H), 2.65(s,3H), 4.7(s,2H), 5.4(s,2H), 6.9-7.0(m,6H), 7.2(d,2H), 7.25-7.45(complex m,12 H), 7.45-7.8(complex m,3H), 7.9(dd,1H).

Provenance & Evidence