Ethyl Acetate → Ethyl 4-[1-[2-hydroxy-2-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl]ethyl]piperidin-4-yl]-2-methylbutanoate

HRID 1059374Notes

Reaction equation

HRID 1059374 reaction equation
[O:1]=[C:2]([C:19]1[CH:20]=[CH:21][C:22]2[S:27][C:26]3[N:28]=[CH:29][CH:30]=[N:31][C:25]=3[NH:24][C:23]=2[CH:32]=1)[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6][CH2:5]1.[BH4-].[Na+].C(OCC)(=O)C>C(O)C>[OH:1][CH:2]([C:19]1[CH:20]=[CH:21][C:22]2[S:27][C:26]3[N:28]=[CH:29][CH:30]=[N:31][C:25]=3[NH:24][C:23]=2[CH:32]=1)[CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][CH2:11][CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 18670229HCID 18670229, compound

Product 1

HCID 18670124Ethyl 4-[1-[2-hydroxy-2-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl]ethyl]piperidin-4-yl]-2-methylbutanoateYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.8 g of ethyl 4-[1-[2-oxo-2-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl]ethyl]piperidin-4-yl]-2-methylbutanoate in ethanol (30 ml) was added 70 mg of sodium borohydride and the resulting mixture was reacted at room temperature for 30 minutes. After adding ethyl acetate, the reaction mixture was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 0.53 g of the title compound as a yellow oily substance.

Workup

  1. customthe resulting mixture was reacted at room temperature for 30 minutes
  2. washthe reaction mixture was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2f80061749f545bd982bb63570a35ed2
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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