Hydrogen Bromide → HCID 66982616, compound

HRID 516253Notes

Reaction equation

HRID 516253 reaction equation
C(OC[N:10]1[C:19]2[C:14](=[CH:15][C:16]3[CH:24]([CH3:25])[CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][CH2:20][C:17]=3[CH:18]=2)[CH2:13][CH2:12][C:11]1=[O:33])C1C=CC=CC=1.Br>>[CH3:25][CH:24]1[C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][C:17]=2[CH2:20][CH2:21][N:22]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:23]1)[NH:10][C:11](=[O:33])[CH2:12][CH2:13]3

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 66982373HCID 66982373, compound

Product 1

HCID 66982616HCID 66982616, compoundYield 104.4%

Procedure

670 mg of t-butyl 1-[(benzyloxy)methyl]-6-methyl-2-oxo-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate was stirred at room temperature for 3.5 hours in a 48% aqueous hydrobromic acid solution. The reaction mixture was extracted with hexane and a side-product, benzyl bromide, was removed. Then, the aqueous layer was alkalified by the addition of a 1 M aqueous sodium hydroxide solution, and 20 ml of tetrahydrofuran was added thereto. To the mixed liquid was added 500 mg of di-t-butyl dicarbonate, followed by stirring at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to obtain 513 mg of t-butyl 6-methyl-2-oxo-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate as a colorless foamed substance.

Workup

  1. extractionThe reaction mixture was extracted with hexane
  2. customa side-product, benzyl bromide, was removed
  3. additionThen, the aqueous layer was alkalified by the addition of a 1 M aqueous sodium hydroxide solution, and 20 ml of tetrahydrofuran
  4. additionwas added
  5. additionTo the mixed liquid was added 500 mg of di-t-butyl dicarbonate
  6. extractionThe reaction mixture was extracted with ethyl acetate
  7. washthe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f3b4f9e033ab49a2b2ec452e577c58db
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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