N-bromobutanimide → tert-butyl [(3S)-7-bromo-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]carbamate

HRID 1670412Notes

Reaction equation

HRID 1670412 reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]=[C:10]1[C@@H:16]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:15][CH2:14][C:13]2[CH:25]=[CH:26][CH:27]=[CH:28][C:12]=2[NH:11]1>CCOC(C)=O>[Br:1][C:26]1[CH:27]=[CH:28][C:12]2[NH:11][C:10](=[O:9])[C@@H:16]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])[CH2:15][CH2:14][C:13]=2[CH:25]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11140356tert-Butyl (S)-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)carbamate

Product 1

HCID 57655890tert-butyl [(3S)-7-bromo-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]carbamateYield 103.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

23.5 g of N-bromosuccinimide (136 mmol) are introduced, at AT, as 4 portions over 3 days, into a 2 l three-necked flask, with stirring and under an argon atmosphere, containing 1.5 l of EtOAc and 8.47 g of 2a (103.0 mmol). The medium is left stirring for an additional overnight period, and washed with 500 ml of HCl (0.5N), 500 ml of a saturated aqueous solution of NaHCO3 and 500 ml of water. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. 38 g of brown foam are obtained. The product is purified by chromatography on a silica cartridge (600 g), elution being carried out with heptane/EtOAc (70/30). 20.46 g of expected product 10a (white solid) are recovered.

Workup

  1. waitThe medium is left
  2. stirringstirring for an additional overnight period
  3. washwashed with 500 ml of HCl (0.5N), 500 ml of a saturated aqueous solution of NaHCO3 and 500 ml of water
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e9de29bdfc8b4fbbb6757de77e52a2b6
Source dataset
uspto-grants-2011_08
Patent number
US07994162B2

Reaction notes

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