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 6763ノート

反応式

HRID 6763 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-20d207dccb154960a6a6d8d38ffea590
出典データセット
uspto-grants-2006_08
特許番号
US07084154B2

反応ノート

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