Tetrahydrofuran → HCID 68292083, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added (2S)-(+)-bornane-10,2-sultam (6.24 gm, 29.0 mmol) and THF (40 mL). The resulting solution was cooled to −78° C. and then n-BuLi (1.6 M in hexanes, 18.6 mL, 29.7 mmol) was added dropwise. The reaction was stirred at −78° C. for 1 hr. Then a solution of (E)-hex-3-enedioyl dichloride in THF (2 mL) was slowly added. After 30 min the dry ice/acetone bath was replaced by an ice bath and the reaction was stirred at 0° C. for 1 hr. After this time, the reaction was quenched by addition of saturated aqueous NH4Cl. The mixture was partitioned between EtOAc and water. The organic phase was isolated, dried over MgSO4, filtered and concentrated. The crude product was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give (3E)-1,6-bis((7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3a,6-methano-2,1-benzothiazol-1(3H,4H)-yl)hex-3-ene-1,6-dione (1.28 gm, 2.38 mmol, 17.2% yield) as a white solid. Anal. Calcd. for C26H38N2O6S2 m/z 538.2. found: 539.1 (M+H)+.

Provenance & Evidence