Réaction #1884961

Équation de réaction

ethyl 1(R)-[1-tert-butoxycarbonyl-4(R)-hydroxypyrrolidine-2(S)-carboxamido]-2(S)-vinylcyclopropanecarboxylate

HCl dioxane

→

ethyl 1(R)-[4(R)-hydroxypyrrolidine-2(S)-carboxamido]-2(S)-vinylcyclopropanecarboxylate hydrochloride

Rendement 97.0%

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction mixture was concentrated in vacuo

Mode opératoire

A stirred slurry of ethyl 1(R)-[1-tert-butoxycarbonyl-4(R)-hydroxypyrrolidine-2(S)-carboxamido]-2(S)-vinylcyclopropanecarboxylate (5.0 g, 13.6 mmol) was treated with 4N HCl/dioxane (20 mL) for 3 h. The reaction mixture was concentrated in vacuo to give 4.5 g (97%) of ethyl 1(R)-[4(R)-hydroxypyrrolidine-2(S)-carboxamido]-2(S)-vinylcyclopropanecarboxylate hydrochloride as a white solid: 1H NMR (300 MHz, CD3OD) δ 1.26 (t, J=7.14 Hz, 3 H), 1.46 (dd, J=9.70, 5.31 Hz, 1 H), 1.80 (dd, J=8.23, 5.31 Hz, 1 H), 2.00-2.15 (m, 1 H), 2.18-2.30 (m, 1 H), 2.45 (dd, J=13.36, 7.50 Hz, 1 H), 3.36-3.48 (m, 1 H), 4.11-4.24 (m, 2 H), 4.44 (dd, J=10.25, 7.68 Hz, 1 H), 4.58-4.65 (m, 1 H), 4.84-4.94 (m, 1 H), 5.17 (d, J=1.83 Hz, 1 H), 5.27-5.42 (m, 1 H), 5.67-5.89 (m, 1 H).

Source