Naphthalene → HCID 70007021, compound

Participants

Reaction Conditions

Reaction Steps

Lithium (175 mg, 25 mmol) was added to a solution of naphthalene (3.2 g, 25 mmol) in tetrahydrofuran (25 mL), and the mixture sonicated for 2 hours. The green solution formed was then slowly added to a solution of (1R*,2R*,5S*,6R*)-2-amino-8-benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octane (Description 8; 2.0 g, 4.6 mmol) in tetrahydrofuran (50 mL), already cooled to −78° C. The mixture was stirred at −78° C. for 1 hour, then quenched with aqueous saturated ammonium chloride solution (50mL). After warming to ambient temperature, the mixture was extracted with ethyl acetate (2×100 mL) and the extracts dried (MgSO4). Concentration in vacuo yielded a solid, which was purified by silica chromatography to give the title compound as a gum (900 mg, 3.1 mmol).

Provenance & Evidence