Tetrahydrofuran → tert-butyl [1-(3,5-difluorobenzyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]carbamate

HRID 1670407Notes

Reaction equation

HRID 1670407 reaction equation
[H-].[Na+].C1COCC1.[O:8]=[C:9]1[CH:15]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14][CH2:13][C:12]2[CH:24]=[CH:25][CH:26]=[CH:27][C:11]=2[NH:10]1.[F:28][C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([F:37])[CH:36]=1)[CH2:32]Br>CCOC(C)=O>[F:28][C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([F:37])[CH:36]=1)[CH2:32][N:10]1[C:11]2[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=2[CH2:13][CH2:14][CH:15]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20])[C:9]1=[O:8]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 5188963,5-Difluorobenzyl bromideHCID 13243501tert-butyl N-(2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)carbamate

Product 1

HCID 57655889tert-butyl [1-(3,5-difluorobenzyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]carbamateYield 137.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

72 mg of sodium hydride in suspension at 60% in oil (1.81 mmol) are introduced, at AT, into a 100 ml round-bottomed flask, with stirring and under an argon atmosphere, containing 20 ml of THF and 0.5 g of 2 (1.81 mmol). The medium is stirred for 1 h and then 0.75 g (3.62 mmol) of 3,5-difluorobenzyl bromide is added. The medium is left stirring at AT overnight. 50 ml of EtOAc are added and the organic phase is washed with 50 ml of water. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. 1 g of a white solid is obtained. After trituration with 20 ml of isopropyl ether and filter-drying, 0.62 g of product 3 (white solid) is obtained.

Workup

  1. stirringThe medium is stirred for 1 h
  2. waitThe medium is left
  3. stirringstirring at AT overnight
  4. washthe organic phase is washed with 50 ml of water
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-9e8482d74fde47bba205094b4e8f8e78
Source dataset
uspto-grants-2011_08
Patent number
US07994162B2

Reaction notes

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