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

HRID 643725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643725
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-868c962852f04d23972c578f926cba82
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700624B2

Notizen zur Reaktion

Wird geladen…