Table 1

1H-NMR of cerivastatin and metabolites 1-a

Protons1-bCerivastatinM-1M-23M-24
δ (ppm)IntegralMultiplicityCoupling Const. (Hz)δ (ppm)IntegralMultiplicityCoupling Const. (Hz)δ (ppm)IntegralMultiplicityCoupling Const. (Hz)δ (ppm)IntegralMultiplicityCoupling Const. (Hz)
CH3 (at CH-C2′)1.246d6.71.236d6.71.233d6.71.233d6.7
1.243d6.71.243d6.7
CH3 (at CH-C6′)1.296d6.71.316d6.71.343d6.71.363d6.7
CH2-OH (at CH-C6′)3.872d5.43.871-c 2ABX16.2; 6.2; 4.8
CH (at C2′)3.361septet6.73.421septet6.73.451septet6.73.451septet6.7
CH (at C6′)3.421septet6.73.501septet6.73.371m3.501m
−CH2OCH3 (at C5′)4.081-c 2AB10.34.111-c 2AB10.3
3.153s3.163s
−CH2OH (at C5′)4.321-c 2AB11.34.331-c 2AB11.3
H-2a2.261dd15.3; 4.42.261dd15.4; 4.42.261dd15.3; 4.52.261dd15.2; 4.3
H-2b2.171dd15.3; 8.02.161dd15.4; 8.02.171dd15.3; 7.92.171dd15.2; 7.8
H-33.741m3.761m3.751m3.751m
H-4a1.521ddd13.8; 9.1; 7.21.521ddd13.7; 8.9; 9.31.521ddd13.7; 8.9; 7.31.511ddd13.7; 8.8; 7.2
H-4b1.271m1.271ddd13.7; 6.5; 4.11.271ddd13.7; 6.4; 4.21.261ddd13.7; 6.3; 4.0
H-54.171m4.171m4.181m4.181m
H-65.331dd16.1; 6.25.331dd16.2; 6.55.341dd16.2; 6.35.341dd16.2; 6.3
H-76.291dd16.1; 1.26.281dd16.2; 1.26.301dd16.2; 1.26.291dd16.2; 1.2
Aromatic7.10–7.184m7.10–7.214m7.13–7.174m7.11–7.224m
  • 1-a Solvent methanol-d4, CD2HOD calibrated at δ = 3.30 ppm.

  • 1-b Numbering used as assigned in scheme FS3.

  • 1-c Centered at.