Methanol → 1,1-Dimethylethyl 3,6-dihydro-4-(hydroxymethyl)-1(2H)-pyridinecarboxylate

HRID 1059353Notes

Reaction equation

HRID 1059353 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14](OC)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].CO.[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([CH2:14][OH:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 118067821-Tert-butyl 4-methyl 1,2,3,6-tetrahydropyridine-1,4-dicarboxylate

Product 1

HCID 225944841,1-Dimethylethyl 3,6-dihydro-4-(hydroxymethyl)-1(2H)-pyridinecarboxylateYield 68.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.6 g of methyl 1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydro-4-pyridinecarboxylate was dissolved in 300 ml of tetrahydrofuran. After adding 4.77 g of lithium tetrahydroborate and then 20 ml of methanol, the resulting mixture was stirred at room temperature for 20 minutes. Saturated ammonium chloride was added to the reaction mixture under ice-cooling and the resulting mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate followed by filtration. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 10.7 g of the title compound as a colorless oily substance.

Workup

  1. temperaturecooling
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed successively with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  6. filtrationfollowed by filtration
  7. distillationAfter distilling off the solvent under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-68d17898bb5c4affac3a58e0d41f0510
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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