Acetone → (1S,9aS) N-[(7-Azidoacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo [3,4-a]indol-1-yl)methyl]acetamide

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Reaction Steps

A mixture of (1S,9aS)N-[(7-chloroacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (EXAMPLE 48, 43 mg) and sodium azide (82 mg) are stirred in aqueous tetrahydrofuran (66%) for 3 days. Acetone (1ml) 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 1000 μ silica preparative plate and developed in methanol/ethylacetate (10/90, 2×) to give the title compound. ##STR3##

Provenance & Evidence