Triethylamine → HCID 22857728, compound

Participants

Reaction Conditions

Reaction Steps

Methanesulfonyl chloride (2.90 mL, 37.5 mmol) and triethylamine (6.50 mL, 46.6 mmol) were added to a solution of the alcohol of Step 5 (15.30 g, 31.3 mmol) in 200 mL of CH2Cl2 at -40° C. and the solution was stirred at -40° C. for 30 min and at 0° C. for 1 hr. Aq. saturated NaHCO3 was then added and the mesylate was extracted in CH2C12, dried over Na2SO4, concentrated, and stripped twice with toluene. To a solution of this mesylate in 240 mL of anhydrous dimethylsulfoxide was added NaCN (7.69, 157 mmol) and the mixture was stirred at room temperature overnight. Water (1 L) was then added, followed by 250 mL of saturated NaHCO3 and the product was extracted in ether, washed with brine, dried over Na2SO4, and purified by flash chromatography on silica with EtOAc:toluene 5:95; yield: 13.43 g (86%).

Provenance & Evidence