Benzyloxyamine hydrochloride → hexahydro-1-[(phenylmethoxy) imino]-2,6-methano-1H-pyrrolizine

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Reaction Steps

Hexahydro-2,6-methano-1H-pyrrolizin-1-one (N. Speckamp, Tetrahedron, 27, 3143 (1971)), 1.45 g, 11.0 mmol, was dissolved in a 1:1 solution of pyridine/ethanol (20 mL). O-Benzyl hydroxylamine hydrochloride (1.85 g, 11.6 mmol) was added and the solution was stirred for 20 hours at room temperature. Removal of the solvents in vacuo afforded a solid which was purified by chromatography on silica gel eluting with 10% MeOH (NH3)/CHCl3 to give hexahydro-1-[(phenylmethoxy) imino]-2,6-methano-1H-pyrrolizine.

Provenance & Evidence