Methanol → HCID 68825515, compound

HRID 1788392Notes

Reaction equation

HRID 1788392 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5]P(OCC)(OCC)=O)C.C[O-].[Na+].CO.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][C:30](=O)[C:29]([CH3:35])([CH3:34])[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>O1CCCC1>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH:31]=[C:30]([CH2:5][C:4]([O:3][CH3:1])=[O:14])[C:29]([CH3:35])([CH3:34])[CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 13345Triethyl phosphonoacetateHCID 10942334Sodium MethoxideHCID 22278899tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 68825515HCID 68825515, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) solution of diethylphosphonoacetic acid ethyl ester (4.4 mL, 24.2 mmol) in tetrahydrofuran (50 mL) under an atmosphere of nitrogen were added a solution of 28% sodium methoxide in methanol (4.6 mL, 26.4 mmol), and then a solution of 3,3-dimethyl-4-oxopiperidine-1-carboxylic acid t-butyl ester (5.0 g, 22.0 mmol) in tetrahydrofuran (10 mL) and stirred for 3 hours at room temperature. After the reaction was completed, the solvent was removed under a reduced pressure and water was added to the residue. The mixture was extracted with ether, washed with water and saturated brine, and dried over anhydrous sodium sulfate. After drying, the extract was filtered and the filtrate was concentrated under a reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent, hexane:ethyl acetate=6:1) to obtain 1.8 g (yield 32.1%) of 4-methoxycarbonylmethylene-3,3-dimethylpiperidine-1-carbxylic acid t-butyl ester (A) and 3.3 g (yield 58.9%) of 4-methoxycarbonylmethyl-3,3-dimethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (B). Each of their physical properties is shown below.

Workup

  1. customthe solvent was removed under a reduced pressure and water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with ether
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter drying
  7. filtrationthe extract was filtered
  8. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-0ecabee530a54afaa5a933f5da3d5975
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

Loading…