Ethyl Acetate → HCID 23122048, compound

HRID 1713558Notes

Reaction equation

HRID 1713558 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20](OCC)=[O:21])[CH2:15][CH2:14]3)=[O:12])[CH2:10][CH:5]2[C:4]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:3]1.[H-].[Li+].[Al+3].[H-].[H-].[H-].C(OCC)(=O)C>O1CCCC1.O>[OH:21][CH2:20][CH2:19][N:16]1[CH2:15][CH2:14][CH:13]([C:11]([N:9]2[CH2:8][CH2:7][N:6]3[C:2](=[O:1])[O:3][C:4]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:5]3[CH2:10]2)=[O:12])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 86761174HCID 86761174, compound

Product 1

HCID 23122048HCID 23122048, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl [4-[(tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-7(1H)-yl)carbonyl]piperidin-1-yl]acetate (0.13 g, 0.26 mmol) in tetrahydrofuran (3 mL) was added aluminum lithium hydride (10 mg, 0.26 mmol) at 0° C., and the mixture was stirred at 0° C. for 30 minutes. An excessive amount of ethyl acetate was added thereto, and the mixture was further stirred at 0° C. for 5 minutes. The reaction solution was diluted with water and then extracted with ethyl acetate. The organic layer was washed with a 1 N aqueous sodium hydroxide solution, water and saturated brine, and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was purified with amino silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=9:1), and then recrystallized from diisopropyl ether-ethyl acetate to obtain the title compound (25 mg, yield 21%).

Workup

  1. stirringthe mixture was further stirred at 0° C. for 5 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a 1 N aqueous sodium hydroxide solution, water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solid was filtered off
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified with amino silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=9:1)
  8. customrecrystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-16edd4784a20472f92b712cebaf41f86
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

Loading…