Water → HCID 67126913, compound

HRID 574902Notes

Reaction equation

HRID 574902 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1.O>CS(C)=O>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH:5]([CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:24][CH2:23]2)[C:4](=[O:8])[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 76322Cyclohexanone, 3,3-dimethyl-HCID 2724254Sodium bis(trimethylsilyl)amideHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate

Product 1

HCID 67126913HCID 67126913, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3,3-Dimethylcyclohexanone (5.60 mL) was added to sodium bis(trimethylsilyl)amide (45.3 mL, 1M in tetrahydrofuran), and the reaction was stirred for 1 hour. tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate (11.1 g) in dimethylsulfoxide (30 mL) was added, and the reaction was stirred at 50° C. for 24 hours. The reaction was cooled, poured into water (300 mL), extracted three times with ether, and the combined extracts were washed three times with water, and brine, dried over Na2SO4, filtered, and concentrated. The crude product was chromatographed on silica gel using 5-20% ethyl acetate in hexanes to provide the title compound.

Workup

  1. stirringthe reaction was stirred at 50° C. for 24 hours
  2. temperatureThe reaction was cooled
  3. extractionextracted three times with ether
  4. washthe combined extracts were washed three times with water, and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was chromatographed on silica gel using 5-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1a239638dbfb4cf989976d95d683ad21
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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