Sodium Sulfate → (5R,7R)-7-(4-(7-methyloctyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one

HRID 1511869Notes

Reaction equation

HRID 1511869 reaction equation
O[C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:24][CH2:23][C@@:17]3([NH:21][C:20](=[O:22])[O:19][CH2:18]3)[CH2:16]2)=[CH:11][CH:10]=1.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO.O.S([O-])([O-])(=O)=O.[Cu+2].[OH-].[OH-].[Pd+2]>[CH3:25][CH:2]([CH3:26])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]2[CH2:24][CH2:23][C@@:17]3([NH:21][C:20](=[O:22])[O:19][CH2:18]3)[CH2:16]2)=[CH:13][CH:14]=1

Participants

7

Reactant 2

HCID 24436Sodium SulfateHCID 57554797(5R,7R)-7-(4-(7-hydroxy-7-methyloctyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one

Product 1

HCID 57554785(5R,7R)-7-(4-(7-methyloctyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-oneYield 54.6%

Reagents, catalysts & solvents 4

HCID 61499Cupric sulfate monohydrateCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a slurry of silica gel (1 g) and copper sulfate hydrate (1 g) in toluene (10 mL) was added (5R,7R)-7-(4-(7-hydroxy-7-methyloctyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one (230 mg, 0.640 mmol). The reaction mixture was heated to 100° C. After 2 days Na2SO4 (approx. 500 mg) was added. After an additional 1 day at 100° C. the reaction mixture was cooled to room temperature and filtered, rinsing with EtOAc. The resulting alkene was added to a slurry of palladium hydroxide on carbon (4.49 mg, 0.032 mmol) in MeOH (10.00 mL). Hydrogen was bubbled through the solution for 5 min and an atmosphere of hydrogen was maintained via balloon. After 15 h the reaction mixture was filtered and concentrated in vacuo. The crude alkane was purified by chromatography on silica gel (EtOAc/Hep) to provide (5R,7R)-7-(4-(7-methyloctyl)phenyl)-3-oxa-1-azaspiro[4.4]nonan-2-one (120 mg, 0.349 mmol, 54.6% yield) as a colorless solid.

Workup

  1. temperatureAfter an additional 1 day at 100° C. the reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washrinsing with EtOAc
  4. customHydrogen was bubbled through the solution for 5 min
  5. temperaturean atmosphere of hydrogen was maintained via balloon
  6. filtrationAfter 15 h the reaction mixture was filtered
  7. concentrationconcentrated in vacuo
  8. customThe crude alkane was purified by chromatography on silica gel (EtOAc/Hep)

Sources & evidence

ORD record
ord-d5b754e4f07547399737832eecebf83b
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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