Ethyl Acetate → 3-Ethyl-2,3,9,10,11,12-hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepine fumarate

HRID 981938Notes

Reaction equation

HRID 981938 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([CH:13]1[C:19](=[O:20])[NH:18][C:17]2=[C:21]3[C:26](=[N:27][C:28]4=[CH:29][CH:30]=[CH:31][C:15](=[C:16]24)[O:14]1)[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH3:12].[OH-:32].[Na+].[C:34]([O:37]CC)(=[O:36])[CH3:35]>O1CCCC1>[C:19]([OH:20])(=[O:32])/[CH:13]=[CH:35]/[C:34]([OH:37])=[O:36].[CH2:11]([CH:13]1[CH2:19][NH:18][C:17]2=[C:21]3[C:26](=[N:27][C:28]4=[CH:29][CH:30]=[CH:31][C:15](=[C:16]24)[O:14]1)[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH3:12]

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 537311453-Ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

Product 1

HCID 677569463-Ethyl-2,3,9,10,11,12-hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepine fumarateYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride in tetrahydrofuran (1M, 14.8 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (1.89 g) in portions, with stirring. After 5 mins, 3-ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.0 g) was added, and the reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 ml) and 10% sodium hydroxide solution (200 ml) were added. The organic phase was separated, dried over magnesium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed (5% triethylamine/toluene). The appropriate fractions were concentrated and treated with fumaric acid to give 4.05 g (74%) of product, mp 210° C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customchromatographed (5% triethylamine/toluene)
  7. concentrationThe appropriate fractions were concentrated
  8. additiontreated with fumaric acid

Sources & evidence

ORD record
ord-baae56e330414faa9cf67d0024ce4499
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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