Pyridine → HCID 86648683, compound

HRID 43734Notes

Reaction equation

HRID 43734 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.N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(OCC)(=O)C>[C:25]([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)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11425480Tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 86648683HCID 86648683, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate [synthesized by the method described in Tetrahedron Lett., 46(3), 447-450 (2005)] (10 g, 38.3 mmol), pyridine (100 mL) and acetic anhydride (18.1 mL, 192 mmol) was stirred at 70° C. overnight. The reaction solution was cooled to room temperature, diluted with ethyl acetate, washed with 1 N hydrochloric acid and brine, and dried over magnesium sulfate. Thereafter, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Elution solvent: hexane/ethyl acetate=4/1) to obtain 9.65 g of the title compound as a colorless oil (83%).

Workup

  1. customsynthesized by the method
  2. washwashed with 1 N hydrochloric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. customThereafter, the solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (Elution solvent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-656e53fa062d4a9c93f7a2d43894e891
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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