Sodium Hydroxide → 8-Benzyl-8-azabicyclo(3.2.1)octan-3-one

Participants

Reaction Conditions

Reaction Steps

2,5-dimethoxytetrahydrofuran (17.1 g, 132.2 mmol) was dissolved in 0.025 M HCl (56 mL) and the mixture was stirred at 0° C. for 16 h. Benzylamine hydrochloride (22.8 g, 158.6 mmol) and 3-oxopentanedioic acid (19.3 g, 132.2 mmol) followed by aqueous sodium acetate (105 mL, 0.69 M). The reaction mixture was warmed to room temperature and stirred for lh then heated to 50° C. for 1.5 h. After cooling back to rt the mixture was basified with sodium hydroxide and extracted with EtOAc (3×) The combined organic portions were dried over sodium sulfate and concentrated. Flash chromatography (450 g silica, 50/1 CH2Cl2/MeOH), gave the desired product. 1H NMR (500 MHz, CDCl3) δ1.65 (m, 2H), 2.05-2.15 (m, 2H), 2.2 (s, 1H), 2.23 (s, 1H), 2.69 (m, 1H), 2.72 (m, 1H), 3.48 (s, 2H), 7.2-7.3 (m, 1H), 7.33-7.4 (m, 4H).

Provenance & Evidence