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Water → (3-(tert-Butoxycarbonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)boronic acid

HRID 645882
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HRID 645882 반응식
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:26]=[CH:25][C:12]3[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17][C:11]=3[CH:10]=2)[O:3]1.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].O>CC(C)=O>[CH3:24][C:21]([O:20][C:18]([N:15]1[CH2:14][CH2:13][C:12]2[CH:25]=[CH:26][C:9]([B:4]([OH:5])[OH:3])=[CH:10][C:11]=2[CH2:17][CH2:16]1)=[O:19])([CH3:22])[CH3:23]
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참가 물질

6

반응물 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 57505869tert-Butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate

생성물 1

HCID 57440296(3-(tert-Butoxycarbonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)boronic acid수율 84.9%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

1,1-Dimethylethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (E264, Step 1) (1.60 g, 4.29 mmol) was dissolved in acetone (25 ml), treated with sodium periodate (2.75 g, 12.9 mmol), ammonium acetate (0.73 g, 9.44 mmol) and water (25 ml) and the resulting mixture was stirred for 18 hours at room temperature. The acetone was removed by evaporation in vacuo and the remaining water layer was extracted with ethyl acetate and dichloromethane. The organic layers were combined, dried under magnesium sulfate and evaporated in vacuo to give the title compound (1.06 g); MS (ES+) m/e 192 [(M+H)—CO2tBu]+.

후처리

  1. customThe acetone was removed by evaporation in vacuo
  2. extractionthe remaining water layer was extracted with ethyl acetate and dichloromethane
  3. customdried under magnesium sulfate
  4. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-4349a7eb67244611accb8753fdc2a560
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07704994B2

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