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

HRID 1027867

반응식

HRID 1027867 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(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.

후처리

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

출처 및 근거

ORD 기록
ord-e717cf9abbdd43409d2b38cfaa1fc7a5
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735411B2

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