Dimethyl acetylenedicarboxylate → 7-Azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylic acid 2,3-dimethyl 7-tert-butyl ester

HRID 723644

반응식

HRID 723644 반응식
[CH3:1][O:2][C:3]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[C:11]([O:15][C:16]([N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>>[CH3:14][C:11]([O:15][C:16]([N:18]1[CH:19]2[CH:20]=[CH:21][CH:22]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]2[C:3]([O:2][CH3:1])=[O:4])=[O:17])([CH3:12])[CH3:13]

참가 물질

3

반응물 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 643494tert-butyl 1H-pyrrole-1-carboxylate

생성물 1

HCID 140854137-Azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylic acid 2,3-dimethyl 7-tert-butyl ester수율 50%

반응 조건

온도
120 °C

실험 절차

Freshly distilled acetylenedicarboxylic acid dimethyl ester (6.7 mL, 54 mmol) and N-(tert-butyloxycarbonyl)-1H-pyrrole (9.0 mL, 54 mmol) were combined and heated at 120° C. for 3 h. Purification by flash chromatography on SiO2 eluting with EtOAc/CH2Cl2 gave 8.3 g (27 mmol, 50%) of compound 31A as a yellow solid.

후처리

  1. customPurification by flash chromatography on SiO2 eluting with EtOAc/CH2Cl2

출처 및 근거

ORD 기록
ord-cf73406a75374ce68bddf715f69afaa4
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141578B2

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