1,2-Dichloroethane → tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate

Participants

Reaction Steps

To a solution of 1-Boc-azetidine-3-carboxylic acid (5.0 g, 24.9 mmol) in DMF (40 mL) was added N,O-dimethylhydroxylamine hydrochloride (2.89 g, 29.8 mmol), EDC (5.55 g, 29.8 mmol), HOBt (3.36 g, 24.9 mmol) and DIPEA (9.82 mL, 54.7 mmol). The reaction was stirred at room temperature for 20 h. The reaction was diluted with water (150 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were washed with water (150 mL) and brine (150 mL), dried over MgSO4 and concentrated under vacuum to afford 4 as a clear colorless oil (6.06 g, 99%); 1H-nmr (400 MHz, CDCl3) δ 4.21-4.11 (m, 2H), 4.05 (t, J=8.0 Hz, 2H), 3.66 (s, 3H), 3.68-3.59 (m, 1H), 3.21 (s, 3H), 1.44 (s, 9H); m/z 189.1 [M−tBu].

Provenance & Evidence