Hydrogen Peroxide → Tert-butyl 4-(3-hydroxypropoxy)piperidine-1-carboxylate

HRID 1816713Notes

Reaction equation

HRID 1816713 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][CH:16]=[CH2:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCCCCCCC.[OH-:27].[Na+].OO>C1COCC1.C(OCC)(=O)C>[OH:27][CH2:17][CH2:16][CH2:15][O:14][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8141NonaneHCID 14798Sodium HydroxideHCID 21990010Tert-butyl 4-(allyloxy)piperidine-1-carboxylate

Product 1

HCID 22494654Tert-butyl 4-(3-hydroxypropoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of N-t-butoxycarbonyl-4-allyloxypiperidine (2.95 g) in THF (15 ml) was added 9-borobicyclo[3.3.1]nonane (9-BBN, 0.5M solution in THF) (51.3 ml) under ice-cooling with stirring, and the mixture was stirred at ambient temperature for 4 hours. The reaction mixture was cooled at 0-5° C., and 3M aqueous sodium hydroxide (20.4 ml) and 30% hydrogen peroxide aqueous solution (20.4 ml) were added the reaction mixture at 0-5° C. The mixture was stirred at ambient temperature for 1 hour. To a reaction mixture was added ethyl acetate (100 ml), and the solution was washed successively with saturated aqueous sodium chloride, 1N-hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (200 ml) eluting with a mixture of dichloromethane and methanol (9:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give 4-(3-hydroxypropyloxy)-N-t-butoxycarbonylpiperidine (3.83 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at ambient temperature for 4 hours
  3. stirringThe mixture was stirred at ambient temperature for 1 hour
  4. washthe solution was washed successively with saturated aqueous sodium chloride, 1N-hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe resulting residue was chromatographed on silica gel (200 ml)
  8. washeluting with a mixture of dichloromethane and methanol (9:1 v/v)
  9. additionThe fractions containing the desired compound
  10. customwere collected
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2c47c6f496254b94a597c067832a9c95
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

Loading…