Dimethyl Sulfate → methyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

HRID 877948Notes

Reaction equation

HRID 877948 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[OH:8][CH2:9][C@H:10]1[O:15][C:14]([CH3:17])([CH3:16])[O:13][C@@H:12]([CH2:18][C:19](O)=[O:20])[CH2:11]1.C(=O)(O)[O-].[Na+]>CO>[OH:8][CH2:9][C@H:10]1[O:15][C:14]([CH3:17])([CH3:16])[O:13][C@@H:12]([CH2:18][C:19]([O:6][CH3:7])=[O:20])[CH2:11]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 18642009Rosuvastatin impurity 42

Product 1

HCID 10560752methyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
27.5 °C

Procedure

Dimethyl sulfate (195 grams) was added to a mixture of 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid (200 grams), methanol (800 ml) and sodium bicarbonate (50 grams) at 0° C. and stirred for 12 hours at 25-30° C. After completion of the reaction, reaction mixture was quenched with water and extracted into methylene chloride. The methylene chloride was distilled off from the reaction mixture under reduced pressure to get the title compound.

Workup

  1. customAfter completion of the reaction, reaction mixture
  2. customwas quenched with water
  3. extractionextracted into methylene chloride
  4. distillationThe methylene chloride was distilled off from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-b0da05687b6e4c50bb4d505940b17605
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

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