Dimethyl Sulfate → HCID 21193434, compound

HRID 1068438Notes

Reaction equation

HRID 1068438 reaction equation
[H-].[K+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=2)([CH2:16][OH:17])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].S(OC)(O[CH3:30])(=O)=O>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=2)([CH2:16][O:17][CH3:30])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 82127Potassium hydrideHCID 21193301HCID 21193301, compound

Product 1

HCID 21193434HCID 21193434, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of potassium hydride (0.40 g, dry weight, 10 mmol; obtained from washing 0.97 g of 35% potassium hydride dispersion in mineral oil with hexanes and drying under a stream of argon) in anhydrous THF (45 mL), N-tert-butoxycarbonyl-4-(3-methylbenzyl)-4-hydroxymethylpiperidine (1.89 g, 5.9 mmol) in THF (15 mL) was added. The resultant mixture was stirred at room temp. for 1 h, and treated with dimethyl sulfate (1.13 mL, 11.9 mmol). The reacting mixture was stirred at room temp. overnight. The product mixture was cooled to 0° C., quenched with water, and diluted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 10% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. customdry weight, 10 mmol
  2. customobtained
  3. washfrom washing 0.97 g of 35% potassium hydride dispersion in mineral oil with hexanes
  4. dry with materialdrying under a stream of argon) in anhydrous THF (45 mL)
  5. customquenched with water
  6. additiondiluted with ethyl acetate
  7. extractionThe organic extract
  8. washwas washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum
  12. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-f31b955555d74da7ab82696cb9b87130
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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