Lithium tri-s-butylborohydride → HCID 19100632, compound

Participants

Reaction Conditions

Reaction Steps

A 50 ml round-bottom flask, equipped with a magnetic stirring bar, septum, and nitrogen inlet, was charged with 220 mg (0.44 mmol, 1.0 equiv) of 1-[2-(2-trityl-tetrazol-5-yl)phenyl]-4-formylcyclohexane (from Step G) and 4 ml THF (over sieves). Into this clear solution, after being cooled down to -25° C., was added 530 μl (1.0M solution in THF, 0.53 mmol, 1.2 equiv) L-Selectride solution. After one hour, another 530 μl of L-Selectride solution was added to push the reaction to completion. The reaction was quenched after 1.5 hours with saturated aqueous sodium bicarbonate solution. Ethyl acetate was added to dissolve the organics. Layers were separated, and the aqueous layer was extracted with 5×10 ml ethyl acetate. The combined organic portion was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, concentrated, and chromatographed on a silica gel column (3 cm×31 cm, 4:6:1=hexane:methylene chloride:ethyl acetate, 1% distilled triethylamine) to afford 180 mg (82%) of the title alcohol: Rf=0.32 (4:6:1=hexane:methylene chloride:ethyl acetate, 1% distilled triethylamine); 1H NMR δ3.71-3.67 (dd, CHCH2OH from one isomer), 3.38-3.32 (dd, CHCH2OH from the other isomer), 3.10-3.00 (tt, CH2CHCH2); 13C NMR δ68.6, 40.2, 40.0, 33.2, 29.4.

Provenance & Evidence