(+/-)-cis-1-Methylethyl 6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane4-acetate → Atorvastatin Impurity 206

HRID 360011Notes

Reaction equation

HRID 360011 reaction equation
[C:1]([CH2:3][C@H:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]([CH2:12][C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[CH2:5]1)#[N:2]>C(O)(=O)C.[Pt](=O)=O>[NH2:2][CH2:1][CH2:3][C@H:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]([CH2:12][C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[CH2:5]1

Participants

4

Reactant 1

HCID 10999646(+/-)-cis-1-Methylethyl 6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane4-acetate

Product 1

HCID 11139823Atorvastatin Impurity 206

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of (±)-cis-1-methylethyl 6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetate, 0.55 g, in glacial acetic acid is hydrogenated with platinum dioxide at 50 pounds per square inch (PSI). Concentration, dilution with ethyl acetate and bicarbonate wash, followed by washing with brine and drying provides 250 mg of (±)-cis-1-methylethyl 6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate. MS 260.1, 244.1

Workup

  1. concentrationConcentration, dilution with ethyl acetate and bicarbonate
  2. washwash
  3. washby washing with brine
  4. customdrying

Sources & evidence

ORD record
ord-eaf7cd71660e4dbeb5861f24a35967a0
Source dataset
uspto-grants-1991_03
Patent number
US05003080

Reaction notes

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