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

HRID 1587157Notes

Reaction equation

HRID 1587157 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-8d3f71ce60ea4638ac634c9305b309b9
Source dataset
uspto-grants-1993_06
Patent number
US05216174

Reaction notes

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