1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 4632592, compound

Participants

Reaction Steps

To a suspension of glycine ethyl ester hydrochloride (21.77 g, 156 mmol) in anhydrous dichloromethane (260 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (55 mL, 368 mmol) was added under nitrogen, which addition turned the suspension clear. Then 2-thiopheneacetyl chloride (19.2 mL, 156 mmol) was added dropwise. After completion of the addition, the flask was warmed to room temperature and the mixture was stirred for 1 hour. Then it was washed with water (260 mL×3), dried and concentrated. A dark brown oil was obtained (31.77 g, yield 89%), which turned into a dark brown solid upon standing. 1H NMR (CDCl3, 500 MHz), δ=7.26 (dd, J=5.0, 1.0 Hz, 1H), 7.01-6.97 (m, 2H), 6.19 (s, 1H), 4.18 (q, J=7.0 Hz, 2H), 4.00 (d, J=5.0 Hz, 2H), 3.83 (s, 2H), 1.26 (t, J=7.0 Hz, 3H).

Provenance & Evidence