Citric Acid → HCID 21193269, compound

HRID 1901088Notes

Reaction equation

HRID 1901088 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]([CH2:24][OH:25])([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].CI.[C:28](O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CS(C)=O>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][C:13]([CH2:24][O:25][CH3:28])([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH2:14][CH2:15]1)=[O:9])([CH3:5])([CH3:6])[CH3:4]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21193307HCID 21193307, compound

Product 1

HCID 21193269HCID 21193269, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. suspension of sodium hydride (19 mg, 0.80 mmol) in 1.5 ml of THF, was added a solution of N-t-butoxycarbonyl-4-hydroxymethyl-4-(2-methylbenzyl)piperidine (200 mg, 0.63 mmol) in 1 ml THF. The mixture was allowed to warm to room temp. To this suspension was added 0.35 ml of anhydrous DMSO and the mixture was heated to 60° C. and stirred 5 h until the solution was almost homogeneous. The reaction mixture was allowed to cool to room temp. and to this solution was added methyl iodide (0.070 ml, 1.12 mmol). The resulting heterogeneous mixture was stirred at room temp. overnight. The reaction mixture was treated with 10% aqueous citric acid and extracted with ether (3×). The combined ether extracts were washed successively with saturated aqueous NaHCO3 and brine, dried (MgSO4), and concentrated in vacuo to a yellow gum. Purification by column chromatography on silica with 9% EtOAc/hexane as eluent afforded the product as a colorless gum.

Workup

  1. temperaturethe mixture was heated to 60° C.
  2. temperatureto cool to room temp. and to this solution
  3. stirringThe resulting heterogeneous mixture was stirred at room temp. overnight
  4. extractionextracted with ether (3×)
  5. washThe combined ether extracts were washed successively with saturated aqueous NaHCO3 and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo to a yellow gum
  8. customPurification by column chromatography on silica with 9% EtOAc/hexane as eluent

Sources & evidence

ORD record
ord-8240e3c4982e494a823b484956307435
Source dataset
uspto-grants-1996_11
Patent number
US05576313

Reaction notes

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