Acetone → HCID 53718121, compound

Participants

Reaction Steps

A mixture of (+/-)-(1S,9aS),(1R,9aR) N-[(7-chloroacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (EXAMPLE 46, 43 mg) and sodium azide (82 mg) are stirred in aqueous tetrahydrofuran (66%) for 3 days. Acetone (1 ml) is added and the mixture was heated in an oil bath (38°-50°) for 8 hours then concentrated to an aqueous layer and extracted with ethylacetate (6×2 ml). The combined organic layers are dried over magnesium sulfate and concentrated to provide the product as as an oil. The oil is taken up in methylene chloride/methanol and then placed on a 1000μ silica preprative plate and developed in methanol/ethylacetate (10/90, 2×) to give the title compound as an oil, NMR (CDCl3, 300 MHz) 7.79, 7.43, 6.45, 4.63, 4.53, 3.75, 3.38, 3.14 and 2.08 δ; IR (CHCl3) 2100, 1760, 1670 and 1360 cm-1.

Provenance & Evidence