Reaction #1884959

Reaction equation

Ethyl 1(R)-tert-butoxycarbonylamino-2(S)-vinylcyclopropanecarboxylate

HCl dioxane

→

ethyl 1(R)-amino-2(S)-vinylcyclopropane carboxylate hydrochloride

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   Otherthe temperature below 40° C

Procedure

Ethyl 1(R)-tert-butoxycarbonylamino-2(S)-vinylcyclopropanecarboxylate (8.5 g, 33.3 mmol) was stirred under an N2 atmosphere with 200 mL of 4N HCl/dioxane (Aldrich) at rt for 3 h. The solvent was removed under reduced pressure keeping the temperature below 40° C. This gave 6.57 g (˜100%) of ethyl 1(R)-amino-2(S)-vinylcyclopropanecarboxylate hydrochloride as a light tan solid. 1H NMR (300 MHz, CD3OD) δ 1.31 (t, J=7.0 Hz, 3 H), 1.69-1.82 (m, 2 H), 2.38 (q, J=8.8 Hz, 1 H), 4.29 (q, J=7.0 Hz, 2 H), 5.22 (d, J=10.3 Hz, 1 H), 5.40 (d, J=17.2 Hz, 1 H), 5.69-5.81 (m, 1 H). MS m/z 156 (M++1).

Source