Potassium Carbonate → tert-Butyl 4-((2-cyclohexyl-2-hydroxy-2-phenylacetyloxy)methyl)-piperidine-1-carboxylate

HRID 1472744Notes

Reaction equation

HRID 1472744 reaction equation
[CH:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([OH:11])[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[CH:12]1([C:7]([OH:11])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([O:10][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:22][CH2:21]2)=[O:9])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 97700(+-)-Cyclohexylphenylglycolic acidHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate

Product 1

HCID 71249173tert-Butyl 4-((2-cyclohexyl-2-hydroxy-2-phenylacetyloxy)methyl)-piperidine-1-carboxylateYield 75%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cyclohexylmandelic acid (885 mg, 3.78 mmol) was added to tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (957 mg, 3.44 mmol) and potassium carbonate (713 mg) in dimethyl formamide (10 mL) at RT with stirring. After 72 hours, the reaction was diluted with ethyl acetate and water. The organic extracts were washed with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated under reduced pressure. The crude reaction mixture was purified by silica gel column chromatography eluting with 0-30% ethyl acetate in iso-hexane to afford the title compound (1.10 g, 75%).

Workup

  1. washThe organic extracts were washed with saturated sodium chloride solution
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude reaction mixture
  6. customwas purified by silica gel column chromatography
  7. washeluting with 0-30% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-a5be84c065104a84a96c78dee796127c
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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