Ethyl (1R,2S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenylcyclopropanecarboxylate → Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, hydrochloride (1:1), (1R,2S)-

HRID 500352

Reaction equation

HRID 500352 reaction equation
C(OC([NH:8][C@:9]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][C@H:10]1[CH:12]=[CH2:13])=O)(C)(C)C.[ClH:19].O1CCOCC1>>[ClH:19].[NH2:8][C@:9]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][C@H:10]1[CH:12]=[CH2:13]

Participants

3

Reactant 2

HCID 10658673Ethyl (1R,2S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenylcyclopropanecarboxylateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 66670028Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, hydrochloride (1:1), (1R,2S)-

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=7.0Hz, 3H), 1.69-1.82 (m, 2H), 2.38 (q, J=8.8Hz, 1H), 4.29 (q, J=7.0Hz, 2H), 5.22 (d, J=10.3Hz, 1H), 5.40 (d, J=17.2Hz, 1H), 5.69-5.81 (m, 1H). MS m/z 156 (M++1).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b10a62a586344cadab5daca883bbc720
Source dataset
uspto-grants-2010_08
Patent number
US07772183B2

Linked notes

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