Imidazole → 4-((Tert-butyldimethylsilyl)oxy)piperidine

HRID 239913Notes

Reaction equation

HRID 239913 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.N1C=CN=C1.[C:13]([Si:17]([CH3:20])([CH3:19])Cl)([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl>[C:13]([Si:17]([CH3:20])([CH3:19])[O:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 79341Piperidin-4-ol

Product 1

HCID 114813284-((Tert-butyldimethylsilyl)oxy)piperidineYield 173.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Scheme 1, step C reagent. To a solution of 4-hydroxypiperidine (2.00 g, 9.89 mmoles) in CH2Cl2 (30 mL) is added 1H-imidazole (2.69 g, 39.55 mmoles) followed by t-butyldimethylchlorosilane (3.58 g, 23.73 mmoles) and the reaction mixture is stirred at room temperature. After 12 hours, the reaction mixture is washed with water, saturated solution of NaHCO3, and brine. The organic layers are combined and dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) over a gradient using 100% CH2Cl2 to 10% 7N ammonia in MeOH/90% CH2Cl2 to afford the title compound (3.69 g, 86.3%). Mass spectrum (m/z): 216.2 (M+1).

Workup

  1. washthe reaction mixture is washed with water, saturated solution of NaHCO3, and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by flash chromatography (silica gel) over a gradient

Sources & evidence

ORD record
ord-2f2b8e21dc6b4c0790d08773d0638d9b
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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