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

HRID 1842702ノート

反応式

HRID 1842702 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7cae381ea07a47cbba3b9eb0876d7494
出典データセット
uspto-grants-2015_02
特許番号
US08946235B2

反応ノート

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