Water → HCID 67126913, compound

HRID 1036005Notes

Reaction equation

HRID 1036005 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-a7a2c5e335cd4ddf9d182e96b2668c0a
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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