Ozone → Tert-butyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate

HRID 265888Notes

Reaction equation

HRID 265888 reaction equation
O=[O+][O-].[C:4]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][CH:19]=C)[CH2:13][CH2:12]1)([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C[OH:22].C(Cl)Cl.[BH4-].[Na+]>CCOC(C)=O>[C:4]([N:11]1[CH2:12][CH2:13][CH:14]([O:17][CH2:18][CH2:19][OH:22])[CH2:15][CH2:16]1)([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5]

Participants

6

Reactant 4

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 21226129Dichloromethane methanolHCID 21990010Tert-butyl 4-(allyloxy)piperidine-1-carboxylate

Product 1

HCID 22030605Tert-butyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ozone was bubbled into a solution of 21-3 (1.5 g, 6.4 mmol) in 2:1 CH3OH/CH2Cl2 (102 mL) at -78° C. After 5 min no starting material remained so oxygen was bubbled through the solution for 15 min to remove excess ozone. NaBH4 (1.7 g, 45 mmol) was added and the cooling bath removed. After 1 h the reaction mixture was concentrated. The residue was diluted with H2O (30 mL) and then extracted with CHCl3 (300 mL). The organic phase was washed with brine (30 mL), dried (MgSO4), and concentrated. Flash chromatography (silica, EtOAc) gave 21-4 as a nearly colorless oil. Rf 0.42 (silica, EtOAc).

Workup

  1. customoxygen was bubbled through the solution for 15 min
  2. customto remove excess ozone
  3. customthe cooling bath removed
  4. concentrationAfter 1 h the reaction mixture was concentrated
  5. additionThe residue was diluted with H2O (30 mL)
  6. extractionextracted with CHCl3 (300 mL)
  7. washThe organic phase was washed with brine (30 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customFlash chromatography (silica, EtOAc) gave 21-4 as a nearly colorless oil

Sources & evidence

ORD record
ord-c26db037aac24724a629cbbc315c22a5
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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