Methylamine → HCID 86594335, compound

Participants

Reaction Steps

To a solution of bicyclo[3,2,1]octane-3,8-dione8-ethylene ketal (53.1 mg, 0.27 mmol, 1.0 eq.) in THF (1.0 mL) at 0° C. was added Et3N (0.11 mL, 2.9 eq.) followed by MeNH2 (2.0 M in THF, 0.21 mL, 1.5 eq.). After stirring at room temperature for 5 minutes, TiCl4 (0.30 mL, 10.0 eq.) was introduced dropwise and the resulting mixture was stirred at 0° C. for 45 minutes. A solution of NaBH4 (53.1 mg, 5.1 eq.) in MeOH (2.0 mL) was then introduced and the resulting mixture was stirred at 0° C. for 1 h. The reaction was quenched with saturated NaHCO3 and the separated aqueous layer was extracted with 3×EtOAc. The combined organic phase was dried over MgSO4, filtered and concentrated to give the crude product, 3-methylamino-bicyclo[3,2,1]octan-8-one ethylene ketal (24.1 mg).

Provenance & Evidence