Acetyl chloride → (1R)-1,3,8,8-Tetramethyl-3-azabicyclo[3.2.1]octane-2,4-dione

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Reaction Steps

To a solution of step 1 intermediate (4.5 g, 21 mmol) in ethyl acetate, acetyl chloride (5.25 mL, 73 mmol) was added and refluxed for 24 hours. After the reaction, ethyl acetate was removed under reduced pressure, crude material purified by column, using ethyl acetate and hexane. (3.7 g) 1H NMR (400 MHz, CDCl3) δ ppm: 0.8 (s, 3H), 0.9 (s, 3H), 1.1 (s, 3H), 1.60-1.61 (m, 1H), 1.71-1.83 (m, 1H), 1.88-1.95 (m, 1H), 2.11-2.2 (m, 1H), 2.65 (d, 1H), 2.91 (s, 3H). m/z (M+H): 196.1.

Provenance & Evidence