Benzyl succinimido carbonate → (3aR,6aR)-Hexahydro-pyrrolo[3,4-b]pyrrole-1,5-dicarboxylic acid 5-benzyl ester 1-tert-butyl ester

HRID 1947378

反応式

HRID 1947378 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]2[CH2:13][NH:14][CH2:15][C@H:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:23][C:24](ON1C(=O)CCC1=O)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]2[CH2:13][N:14]([C:24]([O:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:25])[CH2:15][C@H:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 83172Benzyl succinimido carbonateHCID 29949076rac-tert-butyl (3aR,6aR)-octahydropyrrolo(2,3-c)pyrrole-1-carboxylate

生成物 1

HCID 44221919(3aR,6aR)-Hexahydro-pyrrolo[3,4-b]pyrrole-1,5-dicarboxylic acid 5-benzyl ester 1-tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(3aR,6aR)-Hexahydro-pyrrolo[3,4-b]pyrrole-1-carboxylic acid tert-butyl ester (3.0 g, 12.5 mmole) and N-(benzyloxycarbonyloxy)-succinimide (3.42 g, 13.7 mmole) were mixed in 15 ml of dichloromethane. The mixture was stirred at room temperature overnight and then concentrated under vacuum to provide the crude product. The residue was purified by flash chromatography (20% ethyl acetate in hexane) to provide the title compound. 1H NMR (CDCl3) δ ppm 7.29-7.43 (m, 5H) 5.13 (s, 2H) 4.15-4.33 (m, 1H) 3.39-3.74 (m, 5H) 3.20-3.37 (m, 1H) 2.84-2.96 (m, 1H) 1.92-2.03 (m, 1H) 1.66-1.82 (m, 1H) 1.46 (s, 9H). MS: (M+H)+=347.

後処理

  1. concentrationconcentrated under vacuum
  2. customto provide the crude product
  3. customThe residue was purified by flash chromatography (20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-2f0b4d3161324a32a882329d0e732c31
出典データセット
uspto-grants-2013_03
特許番号
US08399468B2

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