Toluene → HCID 17967911, compound

HRID 2269314Notes

Reaction equation

HRID 2269314 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][C:8]([OH:12])([CH3:11])[CH2:7][N:6]1[S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1)(=[O:15])=[O:14])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH2:23]([O:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([N:6]2[CH2:7][C:8]3([CH3:11])[CH2:9][CH2:10][CH:5]2[C:3](=[O:2])[O:12]3)(=[O:14])=[O:15])=[CH:17][CH:18]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 54329089HCID 54329089, compound

Product 1

HCID 17967911HCID 17967911, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-(4-benzyloxy-benzenesulfonyl)-5-hydroxy-5-methyl-piperidine-2-carboxylic acid methyl ester (0.047 g, 0.11 mmol), p-toluenesulfonic acid (0.010 g, 0.05 mmol) and toluene (2.0 mL) was heated to 90° C. for 2 h. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated in vacuo, giving 0.035 g of 5-(4-Benzyloxy-benzenesulfonyl)-1-methyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one as a colorless oil:

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35e005c2734e4a35b298b05a5af2c449
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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