Citric Acid → HCID 21193269, compound

HRID 1068416Notes

Reaction equation

HRID 1068416 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 suspension of sodium hydride (19 mg, 0.80 mmol) in 1.5 ml of THF, at 0° C. was added a solution of N-t-butoxycarbonyl-4-hydroxymethyl-4-(2-methylbenzyl)piperidine (200 mg, 0.63 mmol) in THF (1 ml). The mixture was allowed to warm to room temperature. To this suspension was added anhydrous DMSO (0.35 ml) and the mixture was heated to 60° C. and stirred 5 hrs until the solution was almost homogeneous. The reaction mixture was allowed to cool to room temperature and methyl iodide (0.070 ml, 1.12 mmol) was added. The resulting heterogeneous mixture was stirred at room temperature for 16 hrs. The reaction mixture was treated with 10% aqueous citric acid and extracted with diethylether. The combined etheral extracts were washed successively with saturated aqueous NaHCO3 brine, dried (MgSO4), and concentrated in vacuo to a yellow gum. Chromatography (SiO2, 9% EtOAc in hexanes) afforded the product as a colorless gum.

Workup

  1. temperaturethe mixture was heated to 60° C.
  2. temperatureto cool to room temperature
  3. stirringThe resulting heterogeneous mixture was stirred at room temperature for 16 hrs
  4. extractionextracted with diethylether
  5. washThe combined etheral extracts were washed successively with saturated aqueous NaHCO3 brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo to a yellow gum

Sources & evidence

ORD record
ord-f7f8d1942d4c4d2eb39358a81257b9b5
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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