Imidazole → 4-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-piperidinone

HRID 1050219Notes

Reaction equation

HRID 1050219 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][C:4](=[O:8])[CH2:3]1.N1C=CN=C1.[Si:14](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.CN(C1C=CN=CC=1)C.C1COCC1>[O:1]([CH:2]1[CH2:7][CH2:6][NH:5][C:4](=[O:8])[CH2:3]1)[Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 112519884-hydroxy-2-Piperidinone

Product 1

HCID 902956574-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-piperidinoneYield 60%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

(±) 4-hydroxypiperidin-2-one (0.80 g, 6.94 mmol) was dissolved in DMF. DMAP (0.085 g, 0.694 mmol) and imidazole (0.92 g, 13.88 mmol) were added. After the resulting mixture was stirred evenly, the solution of TBDPS-Cl (2.3 g, 8.33 mmol) in THF was added and stirred at room temperature overnight. After the reaction completed, the reaction mixture was dried by spinning. Column chromatography afforded colorless oily liquid 0.65 g, yield 60%.

Workup

  1. stirringstirred at room temperature overnight
  2. customthe reaction mixture was dried

Sources & evidence

ORD record
ord-d140cbacf8944a11b2015180f32266f6
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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