Potassium Iodide → 7-(4-Methoxycarbonyl-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester

HRID 222649ノート

反応式

HRID 222649 の反応式
C(OC([CH:8]1[NH:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([OH:19])=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.[C:20](=[O:23])([O-:22])[O-].[K+].[K+].[I-].[K+].Br[CH2:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1>CC(=O)CC>[C:11]([O:22][C:20]([N:14]1[CH2:13][CH2:12][C:15]2[CH:16]=[C:17]([O:19][CH2:29][C:30]3[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=3)[CH:18]=[CH:11][C:10]=2[CH2:9][CH2:8]1)=[O:23])([CH3:18])([CH3:12])[CH3:10]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 686008377-Hydroxy-1,2,4,5-tetrahydro-benzo[c]azepine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 592579207-(4-Methoxycarbonyl-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒2 回

実験手順

7-Hydroxy-1,2,4,5-tetrahydro-benzo[c]azepine-3-carboxylic acid tert-butyl ester (WO 02/40471) (5.27 g, 20.0 mmol), potassium carbonate (8.30 g, 60.0 mmol) and catalytic potassium iodide were suspended in butanone (100 ml). Methyl 4-(bromomethyl)benzoate (5.5 g, 24.0 mmol) dissolved in butanone (50 ml) was added dropwise after which the reaction mixture was stirred at reflux for 24 hours. The reaction mixture was cooled, the solids were filtered and then washed with acetone. The filtrate was concentrated in vacuo and the crude mixture was purified by column chromatography eluting with a mixture of ethyl acetate:hexane (1:4) to afford the title compound (D3). MS (ES+) m/e 344 [(M+H)—CO2tBu]+.

後処理

  1. additionwas added dropwise after which the reaction mixture
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe solids were filtered
  5. washwashed with acetone
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe crude mixture was purified by column chromatography
  8. washeluting with a mixture of ethyl acetate:hexane (1:4)

出典と根拠

ORDレコード
ord-4861129739f24988abb3bd62471a719f
出典データセット
uspto-grants-2012_06
特許番号
US08207331B2

反応ノート

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