反应 #632001

ord-3ceb149eea124d8bb64ae20c80647dae

反应方程式

C=C[C@@H]1C[C@]1(NC(=O)OC(C)(C)C)C(=O)OCC
(1R,2S)N-Boc-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester
C1COCCO1.Cl
HCl dioxane
C=C[C@@H]1C[C@]1(N)C(=O)OCC.Cl
(1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid ethyl ester hydrochloride

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The solvent was removed under reduced pressure
  2. 2
    其他the temperature below 40° C

实验过程

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

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07935670B2uspto-grants-2011_05