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

HRID 1027867ノート

反応式

HRID 1027867 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 (CAS #370880-09-4) (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 reduced pressure 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 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)+ m/z 347.

後処理

  1. concentrationconcentrated under reduced pressure
  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-e717cf9abbdd43409d2b38cfaa1fc7a5
出典データセット
uspto-grants-2014_05
特許番号
US08735411B2

反応ノート

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