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

HRID 641450노트

반응식

HRID 641450 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:28][O:29][C:30]([C:32]1[CH:37]=[CH:36][C:35]([CH2:38]Br)=[CH:34][CH:33]=1)=[O:31]>CC(=O)CC>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([O:19][CH2:38][C:35]3[CH:34]=[CH:33][C:32]([C:30]([O:29][CH3:28])=[O:31])=[CH:37][CH:36]=3)[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 18173274tert-butyl 7-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매2회

실험 절차

7-Hydroxy-1,2,4,5-tetrahydro-benzo[d]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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-be8bc81b09e34b36b249752b3067ab84
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696193B2

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