Potassium Iodide → tert-butyl 7-(benzyloxy)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate

HRID 645780노트

반응식

HRID 645780 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+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>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][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18173274tert-butyl 7-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylate

생성물 1

HCID 57437616tert-butyl 7-(benzyloxy)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate수율 100%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

7-Hydroxy-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester (PCT Int. Appl. (2002), WO 02/40471) (790 mg, 3 mmol), potassium carbonate (1.24 g, 9 mmol) and catalytic potassium iodide were suspended in 2-butanone (20 ml). Benzyl bromide (536 μL, 4.5 mmol) was added and the mixture heated at reflux for 24 hours. The solids were filtered and then washed with acetone. The filtrate was concentrated in vacuo and the crude oil purified by column chromatography, eluting with a mixture of ethyl acetate and hexane (1:4) to afford the title compound (D1) (1.06 g, 100%), 1H NMR (CDCl3) 7.44 (5H, m), 7.03 (1H, d, J 8.1 Hz), 6.77 (1H, s), 6.74 (1H, dd, J 8.1 & 2.4 Hz), 3.49 (4H, m), 2.84 (4H, m), 1.48 (9H, s).

후처리

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe solids were filtered
  4. washwashed with acetone
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe crude oil purified by column chromatography
  7. washeluting with a mixture of ethyl acetate and hexane (1:4)

출처 및 근거

ORD 기록
ord-878b2964d18a42f8a1db701c5973fb52
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704994B2

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