Ethanol → HCID 22857197, compound

HRID 129232Notes

Reaction equation

HRID 129232 reaction equation
[CH3:1][C@@:2]12[C:12]3[C:13]([S:19]([C:22]4[C:27]([CH:28]([CH3:30])[CH3:29])=[CH:26][C:25]([CH:31]([CH3:33])[CH3:32])=[CH:24][C:23]=4[CH:34]([CH3:36])[CH3:35])(=[O:21])=[O:20])=[CH:14][CH:15]=[C:16]4[NH:17][CH:18]=[C:10]([C:11]=34)[CH2:9][C@H:3]1[NH:4][C:5](=O)[CH2:6][O:7]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1][C@@:2]12[C:12]3[C:13]([S:19]([C:22]4[C:23]([CH:34]([CH3:36])[CH3:35])=[CH:24][C:25]([CH:31]([CH3:33])[CH3:32])=[CH:26][C:27]=4[CH:28]([CH3:30])[CH3:29])(=[O:21])=[O:20])=[CH:14][CH:15]=[C:16]4[NH:17][CH:18]=[C:10]([C:11]=34)[CH2:9][C@H:3]1[NH:4][CH2:5][CH2:6][O:7]2

Participants

6

Reactant 4

HCID 702EthanolHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2×HCID 22857194HCID 22857194, compound

Product 1

HCID 22857197HCID 22857197, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-4,6,6a,7,9,10a-hexahydro-10a-methyl-1-(2,4,6-triisopropylphenylsulfonyl)-indolo[3,4-gh][1.4]benzoxazin-8-one (220 mg, 0.43 mmol) in THF (10 ml) was added, while stirring under ice-cooling, LAH (3 equivalents). The mixture was heated for 3 hours under reflux. After completion of the reaction, ethanol was added to the reaction mixture to inactivate the excess amount of LAH. The reaction mixture was added to an ice-cooled saturated aqueous solution of Na2SO4, followed by extraction with ethyl acetate. The extract solution was washed with an aqueous saline solution, followed by drying (anhydrous Na2SO4). The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography, eluting with n-hexane-ethyl acetate (1:5), to afford 106 mg (50%) of the title compound as a syrupy product.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was heated for 3 hours
  3. temperatureunder reflux
  4. additionwas added to the reaction mixture
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract solution was washed with an aqueous saline solution
  7. dry with materialby drying (anhydrous Na2SO4)
  8. distillationThe solvent was distilled off under reduced pressure
  9. washeluting with n-hexane-ethyl acetate (1:5)

Sources & evidence

ORD record
ord-afcdb717072d4f678bcd6e5b4e3997b3
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

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