Acetic Acid → 4-Acetyl-1-azabicyclo[2.2.1]heptane

Participants

Reaction Conditions

Reaction Steps

1-Azabicyclo[2.2.1]hept-4-yl-N-methoxy-N-methyl carboxamide (D21) (10 g, 0.054 mole) was dissolved in dry THF (250 ml) under nitrogen cooled to -40° C. and treated with methyl lithium in ether (55 ml, 1 molar, 0.055 moles). The solution was allowed to warm to room temperature over a period of 1 h. Acetic acid (3.3 ml, leq) was added and the solution concentrated in vacuo to a gum. The residue was partitioned between chloroform and saturated aqueous potassium carbonate solution. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo to a gum which was distilled in vacuo to afford 4-acetyl-1-azabicyclo[2.2.1]heptane (D22) (5.15 g, 0.037 mole, 68%).

Provenance & Evidence