Triethylamine → HCID 67396082, compound

Participants

Reaction Conditions

Reaction Steps

350 mg (1.47 mmol) of the compound from Example 48A were dissolved in 5 ml of THF, the mixture was cooled to 0° C. and 0.20 ml (1.47 mmol) of triethylamine and 0.21 ml (1.61 mmol) of isobutyl chloroformate were added. The mixture was stirred at 0° C. for 1 h. The suspension was then filtered through a Seitz frit into a flask cooled to 0° C., and the residue was rinsed with about 2 ml of THF. With vigorous stirring, the filtrate obtained was then added to a solution, cooled to 0° C., of 166 mg (4.40 mmol) of sodium borohydride in 2 ml of water. After 1 h, 5 ml of saturated sodium bicarbonate solution were added and the mixture was warmed to RT. The mixture was extracted with 15 ml of ethyl acetate. The organic phase was washed successively with in each case 5 ml of saturated sodium bicarbonate solution and saturated sodium chloride solution. After drying over sodium sulfate, the mixture was filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1, then 5:1). This gave 252 mg (63% of theory) of the title compound in a purity of 83%.

Provenance & Evidence