Water → Methyl pyridine-1(2H)-carboxylate

HRID 355675Notes

Reaction equation

HRID 355675 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[BH4-].[Na+].O>CO>[CH3:5][O:4][C:2]([N:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH2:11]1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 4311764Sodium borohydride

Product 1

HCID 11007981Methyl pyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl chloroformate (30.9 mL/400 mmol) was added via syringe to a mixture of pyridine (31.6 g/400 mmol) and sodium borohydride (16.0 g/420 mmol) in methanol (150 mL) at -78° C. Stirred for two hours then poured in to water then extracted with diethyl ether (3×300 mL). The extracts were dried over NaCl/Na2SO4 then evaporated. The residue was purified by preparative chromatography using silica gel eluting with ethyl acetate/hexanes to yield the 1-(methoxycarbonyl)-1,2-dihydropyridine, 1A (20.2 g/130 mmol).

Workup

  1. extractionthen extracted with diethyl ether (3×300 mL)
  2. dry with materialThe extracts were dried over NaCl/Na2SO4
  3. customthen evaporated
  4. customThe residue was purified by preparative chromatography

Sources & evidence

ORD record
ord-c2e4054efa0c4c57b1e29d3bc7f319a7
Source dataset
uspto-grants-1998_11
Patent number
US05834458

Reaction notes

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