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

HRID 2059751

反応式

HRID 2059751 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 mmol) and N-(benzyloxycarbonyloxy)-succinimide (3.42 g, 13.7 mmol) 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 chromatography on silica gel (4:1 hexane-EtOAc, eluant) to provide the title compound. 1H NMR (CDCl3) δ 7.29-7.43 (m, 5 H), 5.13 (s, 2 H), 4.15-4.33 (m, 1 H), 3.39-3.74 (m, 5 H), 3.20-3.37 (m, 1 H), 2.84-2.96 (m, 1 H), 1.92-2.03 (m, 1 H), 1.66-1.82 (m, 1 H), 1.46 (s, 9 H). MS: (DCI+) m/z 347 (M+H).

後処理

  1. concentrationconcentrated under vacuum
  2. customto provide the crude product
  3. customThe residue was purified by chromatography on silica gel (4:1 hexane-EtOAc, eluant)

出典と根拠

ORDレコード
ord-f947bc426ef74ec999bdf2b58c132068
出典データセット
uspto-grants-2012_10
特許番号
US08278313B2

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