Dimethylformamide → 4[(1R)-2-({6-[4-(1,1-Dioxido-2,3-dihydro-1-benzothien-6-yl)butoxy]hexyl}amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of (1R)-2-amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (112 mg) and 6-{3-[(6-bromohexyl)oxy]propyl}-2,3-dihydro-1-benzothiophene 1,1-dioxide and 6-{3-[(6-iodohexyl)oxy]propyl}-2,3-dihydro-1-benzothiophene 1,1-dioxide (370 mg) in dimethylformamide (1 ml) was allowed to stand at room temperature overnight. The solution was concentrated under reduced pressure and the residue was dissolved in ethanol and applied to an SCX-2 cartridge (10 g) eluting with ethanol and then with 10% aqueous ammonia in ethanol. The ammoniacal fractions were concentrated and the residue was dissolved in acetic acid (4 ml) and water (2 ml) and heated to 65° C. for 15 min. The solvents were removed under reduced pressure and the residue was purified on silica SPE cartridge (10 g) eluting with a gradient of 0-15% [10% ammonia in ethanol]-dichloromethane over 17 min. Appropriate fractions were combined and evaporated under reduced pressure. The residue was dissolved in acetic acid and then evaporated to dryness to give the title compound (59 mg) LCMS RT=2.32 min, ES+ve 506 (M+H)+.

Provenance & Evidence