Trifluoromethanesulfonic anhydride → 2-(tert-butyloxycarbonyl)-5-trifluoromethanesulfonyloxy-2,3-dihydro-1H-isoindole

HRID 1059721노트

반응식

HRID 1059721 반응식
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[C:16]([O:20][C:21]([N:23]1[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28](O)[CH:29]=2)[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C(N(CC)CC)C>[C:16]([O:20][C:21]([N:23]1[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:29]=2)[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

참가 물질

4

반응물 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 18630963tert-butyl 5-hydroxy-2,3-dihydro-1H-isoindole-2-carboxylate

생성물 1

HCID 186309682-(tert-butyloxycarbonyl)-5-trifluoromethanesulfonyloxy-2,3-dihydro-1H-isoindole

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

Trifluoromethanesulfonic anhydride (9.6 ml) was added to a solution of 2-(tert-butyloxycarbonyl)-5-hydroxy-2,3-dihydro-1H-isoindole (12.2 g) and triethylamine (8.7 ml) at −20° C. under argon. The reaction was stirred overnight at room temperature, then the crude product isolated by extraction and chromatographed to give 2-(tert-butyloxycarbonyl)-5-trifluoromethanesulfonyloxy-2,3-dihydro-1H-isoindole (12.7 g), which was dissolved in DMF (180 ml). To this solution was added zinc cyanide (3.7 g) and tetrakis-triphenylphosphine palladium (0) (3.7 g) and the mixture was heated at 100° C. for 4 h. Work-up and chromatography on silica gel gave the title compound as a solid (7.6 g, 83%).

후처리

  1. customthe crude product isolated by extraction
  2. customchromatographed

출처 및 근거

ORD 기록
ord-234604bb21624792bf73897584b06392
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521638B1

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