1,4-Dioxane hydrochloride → (1R,2S)-ethyl 1-((3R,5S)-3-hydroxypyrrolidine-5-carboxamido)-2-vinylcyclopropanecarboxylate hydrochloride

HRID 500354

Reaktionsgleichung

Reaktionsgleichung von HRID 500354
C(OC([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([NH:16][C@:17]1([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:19][C@H:18]1[CH:20]=[CH2:21])=[O:15])=O)(C)(C)C.[ClH:27].O1CCOCC1>>[ClH:27].[OH:13][C@H:11]1[CH2:12][NH:8][C@H:9]([C:14]([NH:16][C@:17]2([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:19][C@H:18]2[CH:20]=[CH2:21])=[O:15])[CH2:10]1

Komponenten

3

Edukt 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57892908(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Produkt 1

HCID 67330424(1R,2S)-ethyl 1-((3R,5S)-3-hydroxypyrrolidine-5-carboxamido)-2-vinylcyclopropanecarboxylate hydrochlorideAusbeute 97 %

Versuchsvorschrift

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=7.14Hz, 3H), 1.46 (dd, J=9.70, 5.31Hz, 1 H), 1.80 (dd, J=8.23, 5.31Hz, 1H), 2.00-2.15 (m, 1H), 2.18-2.30 (m, 1H), 2.45 (dd, J=13.36, 7.50Hz, 1H), 3.36-3.48 (m, 1H), 4.11-4.24 (m, 2H), 4.44 (dd, J=10.25, 7.68Hz, 1H), 4.58-4.65 (m, 1H), 4.84-4.94 (m, 1H), 5.17 (d, J=1.83 Hz, 1H), 5.27-5.42 (m, 1H), 5.67-5.89 (m, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dd00066252364e2c963453505fece32f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772183B2

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