6-methoxy-1-methylene-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester → 7-Methoxy-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepine-3-carboxylic acid benzyl ester

HRID 6763노트

반응식

HRID 6763 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=2)[C:12]1=[CH2:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=[O:26])C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[CH:17]=[C:16]([O:21][CH3:22])[CH:15]=[CH:14][C:13]=2[CH2:23][C:12]1=[O:26])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 138591896-methoxy-1-methylene-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl esterHCID 178418268HCID 178418268, 화합물

생성물 1

HCID 235442487-Methoxy-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepine-3-carboxylic acid benzyl ester수율 28.8%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of 6-methoxy-1-methylene-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (0.66 g) in 20 mL of glacial acetic acid was added lead tetraacetate (1 g). The reaction was stirred overnight, then quenched by the addition of 2 mL of glycerol. The volatile material was evaporated and the resulting residue was partitioned between 50 mL of saturated sodium chloride and 50 mL of dichloromethane. The aqueous phase was re-extracted with 50 mL more dichloromethane and the combined extracts were dried over sodium sulfate. The volatile material was evaporated and chromatography (20% ethyl acetate in hexanes) yielded 0.20 g of 7-methoxy-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepine-3-carboxylic acid benzyl ester.

후처리

  1. customquenched by the addition of 2 mL of glycerol
  2. customThe volatile material was evaporated
  3. customthe resulting residue was partitioned between 50 mL of saturated sodium chloride and 50 mL of dichloromethane
  4. extractionThe aqueous phase was re-extracted with 50 mL more dichloromethane
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. customThe volatile material was evaporated

출처 및 근거

ORD 기록
ord-20d207dccb154960a6a6d8d38ffea590
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084154B2

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