Imidazole → 3-({[tert-Butyl(diphenyl)silyl]oxy}methyl)piperidin-2-one

HRID 218532Notes

Reaction equation

HRID 218532 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][C:4]1=[O:9].N1C=CN=C1.[Si:15](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[Si:15]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][C:4]1=[O:9])([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 108879333-(Hydroxymethyl)piperidin-2-one

Product 1

HCID 594107813-({[tert-Butyl(diphenyl)silyl]oxy}methyl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.00 g (38.7 mmol) of 3-hydroxymethylpiperidin-2-one in 40 ml of N,N-dimethylformamide is admixed successively with 3.16 g (46.5 mmol) of imidazole, and dropwise with 11 ml (42.6 mmol) of tert-butyl(diphenyl)silyl chloride. After stirring at RT for 3 hours, the mixture is admixed with approx. 400 ml of water and extracted three times with ethyl acetate. The combined organic extracts are washed successively with saturated ammonium chloride solution, water and saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the mixture is filtered and the filtrate is freed of the solvent under reduced pressure. The resulting residue is purified by suction filtration through silica gel with 20:1→1:1 cyclohexane/ethyl acetate as the eluent. This affords 9.43 g (66% of theory) of the title compound.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts are washed successively with saturated ammonium chloride solution, water and saturated sodium chloride solution
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationthe mixture is filtered
  5. filtrationThe resulting residue is purified by suction filtration through silica gel with 20:1→1:1 cyclohexane/ethyl acetate as the eluent

Sources & evidence

ORD record
ord-70456572dd694a54acf5686577c24660
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Reaction notes

Loading…