Ethyl (1S,2R)-1-{[(tert-butoxy)carbonyl]amino}-2-ethenylcyclopropane-1-carboxylate → ethyl (1S,2R)-1-amino-2-vinyl-cyclopropanecarboxylate;hydrochloride

HRID 544816Notes

Reaction equation

HRID 544816 reaction equation
[CH2:1]([O:3][C:4]([C@:6]1([NH:11]C(OC(C)(C)C)=O)[CH2:8][C@@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].[ClH:19].O1CCOCC1>>[ClH:19].[CH2:1]([O:3][C:4]([C@:6]1([NH2:11])[CH2:8][C@@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 16067766Ethyl (1S,2R)-1-{[(tert-butoxy)carbonyl]amino}-2-ethenylcyclopropane-1-carboxylateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 69670783ethyl (1S,2R)-1-amino-2-vinyl-cyclopropanecarboxylate;hydrochloride

Procedure

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).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-418cbd4d8ab2499d83dc77cbe95e049a
Source dataset
uspto-grants-2011_05
Patent number
US07935670B2

Reaction notes

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