HCID 22006215, compound → HCID 22006218, compound

HRID 323579Notes

Reaction equation

HRID 323579 reaction equation
[CH:1]1([CH:7]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([CH:18]([O:21][CH3:22])[O:19][CH3:20])[NH:10][C:9]([CH:23]([O:26][CH3:27])[O:24][CH3:25])=[C:8]2[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CC(C)=O.O>[CH:1]1([C:7]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([CH:18]([O:19][CH3:20])[O:21][CH3:22])[N:10]=[C:9]([CH:23]([O:26][CH3:27])[O:24][CH3:25])[C:8]=2[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 22006215HCID 22006215, compound

Product 1

HCID 22006218HCID 22006218, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of diethyl 4-cyclohexyl-2,6-bis(dimethoxymethyl)-1,4-dihydropyridine-3,5-dicarboxylate (30.7 g, 67.54 mmol) in acetone (450 mL) was added a solution of ceric ammonium nitrate (75.05 g, 135.08 mmol) in water (125 mL) fairly rapidly at room temperature. After stirring for 10 minutes, the resulting solution was concentrated to remove the acetone. Water (300 mL) was added and the mixture was extracted with CH2Cl2 (3×500 mL). The organic phase was washed with brine (600 mL), dried (MgSO4), and evaporated to afford 29.23 g of diethyl 4-cyclohexyl-2,6-bis(dimethoxymethyl)pyridine-3,5-dicarboxylate as an oil. The oil was chromatographed on silica gel using hexane/ethyl acetate mixtures to give single spot material: 1H NMR (CDCl3) δ 5.37 (s, 2H) 4.32 (q, J=7.2 Hz, 4H) 3.33 (s, 12H) 2.4-2.6 (m, 1H) 1.0-1.8 (m, 16H); 13C NMR (CDCl3) δ 167.79, 153.25, 151.44, 128.68, 104.01, 61.51, 54.41, 52.18, 44.41, 31.10, 27.19, 25.85, 14.04; MS (HR-ESI) m/z 460.2534 [M+Li]+ (460.2523 calcd for C23H35NO8Li).

Workup

  1. concentrationthe resulting solution was concentrated
  2. customto remove the acetone
  3. additionWater (300 mL) was added
  4. extractionthe mixture was extracted with CH2Cl2 (3×500 mL)
  5. washThe organic phase was washed with brine (600 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-c9bcfcc8c2e54870b440fb7b0cf80f0d
Source dataset
uspto-grants-2001_04
Patent number
US06214817B1

Reaction notes

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