Dimethyl Sulfoxide → tert-Butyl 3-oxo-2-phenylpiperidine-1-carboxylate

HRID 2210704Notes

Reaction equation

HRID 2210704 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([OH:24])[CH:19]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH:19]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 215840931-t-Butyloxycarbonyl-3-hydroxy-2-phenylpiperidine

Product 1

HCID 11414684tert-Butyl 3-oxo-2-phenylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (1 ml) was added dropwise to a solution of methyl sulphoxide (0.82 ml) in anhydrous dichloromethane (4 ml) at -78° C. under a nitrogen atmosphere. A solution of 1-t-butoxycarbonyl-3-hydroxy-2-phenyl piperidine (1.6 g, Example 2c) in anhydrous dichloromethane (10 ml) was added, and the reaction stirred for 1.75 h before triethylamine (4 ml) was added and the reaction allowed to warm to room temperature. The reaction was partitioned between ethyl acetate and water, the organic phase washed with brine, dried and evaporated in vacuo to provide 1-t-butoxycarbonyl-2-phenylpiperidin-3-one as an oil.

Workup

  1. additionwas added
  2. customThe reaction was partitioned between ethyl acetate and water
  3. washthe organic phase washed with brine
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-22abd714c05f4eca84859375dad525dd
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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