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

HRID 1842702노트

반응식

HRID 1842702 반응식
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

참가 물질

4

반응물 2

HCID 11084330Ethyl allyl(2-oxoethyl)carbamate2회HCID 28897015N-((1R)-1-Phenylethyl)glycine2회

생성물 1

HCID 71711109(3aR,6aR)-Ethyl 1-((R)-1-phenylethyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate수율 38.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7cae381ea07a47cbba3b9eb0876d7494
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946235B2

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