(S)-(-)-1-(2-Methoxybenzoyl)-2-pyrrolidinemethanol → Anthracene

Participants

Reaction Steps

We were able to successfully load representative primary alcohols to silane resin VIIIa and cleave the resins to afford high yields of alcohol products (Scheme 13). In a typical experiment, 200 mg PS-DES-silane resin was combined with a DCM solution of 1.7 mg of Rh2 (pfb)4 in 10 mL round bottle flask under argon. Then 66 mg of (s)-(-)-1-(2-methoxybenzoyl)-2-pyrrolidinemethanol was added at room temperature and the reaction was monitored by IR. After 3 hrs, the reaction was complete (as evidenced by the disappearance of the Si-H stretch at 2100 cm-1), the reaction mixture was filtered, and washed with 3×DCM, 2×toluene, 2×THF/H2O (1:1), 3×THF. The product was dried under vacuum in a dessicator. This product was then treated with AcOH/THF/H2O (6:6:1) for 12 hrs and the filtrate was concentrated by speedvac (rt, 80 mins) to obtain alcohol with 99.3% yield (GC, anthracene as internal standard).

Provenance & Evidence