Reacción #631998

ord-418cbd4d8ab2499d83dc77cbe95e049a

Ecuación de reacción

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

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ConcentraciónThe reaction mixture was concentrated

Procedimiento

The product of Step 2 (9.39 g, 36.8 mmol) was dissolved in 4N HCl/dioxane (90 mL, 360 mmol) and was stirred for 2 hours at room temperature. The reaction mixture was concentrated to provide (1R,2S)/(1S,2R) 1-amino-2-vinylcyclopropane carboxylic acid ethyl ester hydrochloride in quanitative yield (7 g, 100%). 1H NMR (methanol-d4) δ 1.32 (t, J=7.1, 3H), 1.72 (dd, J=10.2, 6.6 Hz, 1H), 1.81 (dd, J=8.3, 6.6 Hz, 1H), 2.38 (q, J=8.3 Hz, 1H), 4.26-4.34 (m, 2H), 5.24 (dd, 10.3, 1.3 Hz, 1H) 5.40 (d, J=17.2, 1H), 5.69-5.81 (m, 1H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07935670B2uspto-grants-2011_05