Ceric ammonium nitrate → 5-Cyclohexyl-2-(3-hydroxy-propyl)-morpholin-3-one

HRID 579173Notes

Reaction equation

HRID 579173 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][CH:10]1[O:15][CH2:14][CH:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[N:12](CC2C=CC(OC)=CC=2)[C:11]1=[O:31])(C)(C)C.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>CC#N.O.CCOC(C)=O>[CH:16]1([CH:13]2[NH:12][C:11](=[O:31])[CH:10]([CH2:9][CH2:8][CH2:7][OH:6])[O:15][CH2:14]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 2

HCID 180504Ceric ammonium nitrate2×HCID 666846652-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-one

Product 1

HCID 666849885-Cyclohexyl-2-(3-hydroxy-propyl)-morpholin-3-oneYield 66.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-one (400 mg, 0.84 mmol, 1.0 equiv) in CH3CN (0.3 mL) and water (0.3 mL) was added CAN (922 mg, 1.68 mmol, 2.0 equiv). The mixture was stirred at room temperature for 1 hour then second portion of CAN (900 mg) was added. After stirred at room temperature for 1 hour, the reaction mixture was diluted with EtOAc and the phases were separated. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography, EtOAc/heptane 50% to 100% EtOAc to give 5-cyclohexyl-2-(3-hydroxy-propyl)-morpholin-3-one 134 mg.

Workup

  1. stirringAfter stirred at room temperature for 1 hour
  2. customthe phases were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography, EtOAc/heptane 50% to 100% EtOAc

Sources & evidence

ORD record
ord-9c264765e4e044febc1b5373cc5e4036
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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