Triethylamine → (R)-4-Ethylamino-3,4-dihydro-2-(2-hydroxyethyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide

Participants

Reaction Steps

To a stirred solution of (R)-(+)-4-Ethylamino-3,4-dihydro-2-(2-methoxyethyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide hydrochloride (6.03 g, 15.0 mmol) in 1,2-dichloroethane (50 mL) was added triethylamine (210 mL, 1.5 mmol) followed by bromodimethylborane (5.79 mL, 59.0 mmol) at 0° C. After 4 h at room temperature, the reaction was quenched by adding a saturated aqueous solution of sodium bicarbonate; this mixture was extracted with ethyl acetate (4×50 mL). The combined extracts were washed with brine (20 mL), dried (MgSO4) and evaporated to give the desired alcohol product as a syrup (4.8 g, 91%).

Provenance & Evidence