Acetic Acid → Ethyl 10-(benzyl(ethyl)amino)-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate

HRID 1093084Notes

Reaction equation

HRID 1093084 reaction equation
Cl.[NH2:2][C:3]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][N:5]1[C:12](=[O:30])[C:13]([O:21][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:23])=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=[C:4]21.C(N([CH2:36][CH3:37])CC)C.[CH:38](=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CC(O)=O.[BH3-]C#N.[Na+].C(=O)C>ClCCCl>[CH2:38]([N:2]([CH2:36][CH3:37])[C:3]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][N:5]1[C:12](=[O:30])[C:13]([O:21][C:22]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:23])=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=[C:4]21)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 240BenzaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 66588778Ethyl 10-amino-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate hydrochloride

Product 1

HCID 57905266Ethyl 10-(benzyl(ethyl)amino)-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of Ethyl 10-amino-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate hydrochloride (200 mg, 0.461 mmol) in 1,2-dichloroethane (10 mL) was added triethylamine (0.064 mL, 0.461 mmol) and the resulting mixture stirred for 5 min. Benzaldehyde (0.186 mL, 1.844 mmol), AcOH (0.053 mL, 0.922 mmol) and NaCNBH3 (87 mg, 1.383 mmol) were then added and the mixture stirred for 6 h. Acetaldehyde (0.182 mL, 3.23 mmol) was then added to the reaction and the this was stirred at room temperature for 16 h. The mixture was then quenched with sat. NaHCO3 and extracted with dichloromethane, dried (Na2SO4), filtered and concentrated to afford title compound.

Workup

  1. stirringthe mixture stirred for 6 h
  2. stirringthe this was stirred at room temperature for 16 h
  3. customThe mixture was then quenched with sat. NaHCO3
  4. extractionextracted with dichloromethane
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cb8c9b20c93e408c93601cdf83478456
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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