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

HRID 893489Notes

Reaction equation

HRID 893489 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, 244.1 200 MHz NMR (CDCl3) δ1.25 (d, 6H, J=7 Hz), 1.32 (m, 1H), 1.36 (s, 3H), 1.45 (s, 3H), 1.60 (m, 1H), 2.33 (dd, 1H, J=15, 6 Hz), 2.49 (dd, 1H, J=15, 6 Hz), 2.85 (br t, 2H, J=6 Hz), 3.40 (br s, 2H), 4.00 (m, 1H), 4.29 (m, 1H), 12.03 (septet, 1H, J=7 Hz).

Workup

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

Sources & evidence

ORD record
ord-f593b10d7559487c820034dae7eed79e
Source dataset
uspto-grants-1992_06
Patent number
US05124482

Reaction notes

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