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

HRID 641546

Reaction equation

HRID 641546 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-6bcde8c7fe2b45cea7c2acd864248050
Source dataset
uspto-grants-2010_04
Patent number
US07696193B2

Linked notes

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