Hexane → HCID 57202916, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of the (S,S) isomer product of Example 36 (0.91 g., 2.7 mmol.) in water maintained at 0° C. under argon was treated with ammonium hydroxide (5M solution, 10 mL, 50 mmol.) and stirred for 5 minutes. The reaction was quenched at 0° C. with 140 mL of 10% potassium bisulfate and then extracted with ethyl acetate (4×). The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo to yield 1.0 g. of a yellow solid. The crude reaction product was triturated with hexane:ethyl acetate to yield 0.78 g. of the title (S,S) isomer product as an off white solid; m.p. 155°-156° C., TLC Rf =0.18 (ethyl acetate:hexane:acetic acid, 100:100:1). [α]D =+26.1° (c=0.81, methanol).

Provenance & Evidence