Sodium borohydride → Methyl 1-methyl-1,2,3,6-tetrahydropyridine-4-carboxylate

HRID 1702985Notes

Reaction equation

HRID 1702985 reaction equation
[I-].[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][N+:9]([CH3:12])=[CH:8][CH:7]=1)=[O:5].[BH4-].[Na+]>CO>[CH3:12][N:9]1[CH2:8][CH:7]=[C:6]([C:4]([O:3][CH3:2])=[O:5])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 129454874-(Methoxycarbonyl)-1-methylpyridin-1-ium iodide

Product 1

HCID 40462Methyl 1-methyl-1,2,3,6-tetrahydropyridine-4-carboxylateYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A suspension of 1.385 kg of 4-methoxycarbonyl-1-methylpyridinium iodide in 25 liters of dry methanol was stirred and cooled to 5° C. and 700 g of sodium borohydride were added thereto in portions over 1 hour with the temperature held at 5°-10° C. When the addition was complete, the resultant solution was stirred at room temperature for another hour and was then concentrated to 5 to 7 liters. 25 liters of water were added thereto followed by addition of 2 kg of solid sodium carbonate. The solution thus obtained was extracted 3 times with 2.5 liters of chloroform and the organic phase was dried over Na2SO4 and was evaporated to dryness. The residual oil was distilled to obtain 583 g of methyl 1,2,3,6-tetrahydro-1-methylisonicotinate (67.1% yield) boiling at 78° C. at 1 mm Hg.

Workup

  1. additionWhen the addition
  2. concentrationwas then concentrated to 5 to 7 liters
  3. addition25 liters of water were added
  4. additionthereto followed by addition of 2 kg of solid sodium carbonate
  5. customThe solution thus obtained
  6. extractionwas extracted 3 times with 2.5 liters of chloroform
  7. dry with materialthe organic phase was dried over Na2SO4
  8. customwas evaporated to dryness
  9. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-132792ff57d84bc1809c431c9a122d32
Source dataset
uspto-grants-1982_09
Patent number
US04350697

Reaction notes

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