Methyl benzilate → HCID 10616048, compound

HRID 551376

Reaction equation

HRID 551376 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([OH:8])[CH2:3]1.C[O:10][C:11](=O)[C:12]([OH:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Na]>C1CCCCC1>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([O:8][C:11](=[O:10])[C:12]([OH:25])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 66159Methyl benzilateHCID 5360545Sodium2×HCID 6994421(3R)-1-methylpiperidin-3-ol

Product 1

HCID 10616048HCID 10616048, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of (R)-1-methyl-piperidine-3-ol (4.61 g, 0.040 mol) and hydroxy-diphenyl-acetic acid methyl ester (9.63 g, 0.040 mol) in cyclohexane (50 ml) is added preactivated 4A molecular sieves and the mixture heated to 50° C. Sodium metal (50 mg) is then added and the resulting mixture heated to reflux. After 1 hour further sodium (50 mg) is added and reflux maintained for 5 hours. Concentration, re-dissolution in chloroform and washing with water followed by brine, drying over magnesium sulphate, filtration and evaporation gives a crude product. Purification by vacuum flash silica chromatography (gradient elution: DCM to DCM:methanol 20:1) gives, after evaporation, the title product as a foam.

Workup

  1. additionis added
  2. temperaturethe resulting mixture heated to reflux
  3. temperaturereflux
  4. temperaturemaintained for 5 hours
  5. concentrationConcentration, re-dissolution in chloroform
  6. washwashing with water
  7. dry with materialdrying over magnesium sulphate, filtration and evaporation

Sources & evidence

ORD record
ord-32f4808f27494b97ad8673756002bbd2
Source dataset
uspto-grants-2011_05
Patent number
US07947730B2

Linked notes

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