Dimethyl Sulfate → 1-Boc-3,4,4-trimethoxypiperidine

HRID 643725Notes

Reaction equation

HRID 643725 reaction equation
[OH:1][CH:2]1[C:7]([O:10][CH3:11])([O:8][CH3:9])[CH2:6][CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1.O1CCC[CH2:20]1.CC(C)([O-])C.[K+].S(OC)(OC)(=O)=O>C(OCC)(=O)C.O>[CH3:20][O:1][CH:2]1[C:7]([O:8][CH3:9])([O:10][CH3:11])[CH2:6][CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 11425480Tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 592630891-Boc-3,4,4-trimethoxypiperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared by taking tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate (702 mg, 0.00269 mol) in Tetrahydrofuran (10 mL, 0.1 mol) at 0° C. and adding in Potassium tert-butoxide (15 mL, 0.015 mol). The reaction was stirred for 20 min and then Dimethyl sulfate (0.56 mL, 0.006 mol) was added and the temperature raised to ambient temperature. After stirring overnight the reaction mixture was poured into water and ethyl acetate. The organic layers were separated, dried and concentrated in vacuo to afford an oil which was used as-is (424 mg, 99%) MS calculated for C13H25NO5: (M+H) 276; found 276.1.

Workup

  1. customat 0° C.
  2. stirringAfter stirring overnight the reaction mixture
  3. customThe organic layers were separated
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto afford an oil which

Sources & evidence

ORD record
ord-868c962852f04d23972c578f926cba82
Source dataset
uspto-grants-2010_04
Patent number
US07700624B2

Reaction notes

Loading…