Ethyl allyl(2-oxoethyl)carbamate → (3aR,6aR)-Ethyl 1-((R)-1-phenylethyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

HRID 1842702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842702
O=[CH:2][CH2:3][N:4]([CH2:10][CH:11]=[CH2:12])[C:5](=[O:9])[O:6][CH2:7][CH3:8].[C:13]1([C@H:19]([NH:21][CH2:22]C(O)=O)[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[C:13]1([C@H:19]([N:21]2[C@@H:2]3[C@@H:11]([CH2:10][N:4]([C:5]([O:6][CH2:7][CH3:8])=[O:9])[CH2:3]3)[CH2:12][CH2:22]2)[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

4

Edukt 2

HCID 11084330Ethyl allyl(2-oxoethyl)carbamate2×HCID 28897015N-((1R)-1-Phenylethyl)glycine2×

Produkt 1

HCID 71711109(3aR,6aR)-Ethyl 1-((R)-1-phenylethyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylateAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of ethyl N-(2-oxoethyl)-N-prop-2-enylcarbamate (Intermediate 41, 466 g, 2.7 mol) and 2-{[(1R)-1-phenylethyl]amino}acetic acid (Intermediate 43A, 490 g, 2.7 mol) in toluene (4 L) was refluxed overnight. The resulting mixture was filtered and the filtrate was concentrated in vacuo. Purification by FCC, eluting with 10:1 petrol-EtOAc, gave the title compound (300 g, 38%) as red oil; 1H NMR: (CDCl3) 1.10-1.40 (8H, m), 1.55 (1H, m), 1.90 (1H, m), 2.45 (1H, m), 2.77 (1H, m), 3.20-3.65 (5H, m), 4.10-4.20 (2H, m), 7.25-7.38 (5H, m).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. filtrationThe resulting mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification by FCC
  5. washeluting with 10:1 petrol-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-7cae381ea07a47cbba3b9eb0876d7494
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946235B2

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