tert-Butanol → 2-Chloro-5-(2,3-dihydroxypropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Participants

Reaction Steps

2-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (prepared as described in Example 5a) (1.99 g), tert-butanol (40 mL) and water (40 mL) were stirred together under nitrogen and AD-mix-α was added. The mixture was then stirred at room temperature for 20 hours. Sodium sulfite (2 g) was added and the mixture was stirred for 10 minutes. Water (100 mL) and ethyl acetate (100 mL) were then added. The layers were separated and the aqueous layer was further extracted with ethyl acetate (2×100 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude product. Purification was performed by column chromatography eluting with 5:95 methanol/ethyl acetate to give the sub-titled compound as a solid (1.77 g).

Provenance & Evidence