Methyl coumalate → (R)-methyl 1-(2-hydroxypropyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 2370814Notes

Reaction equation

HRID 2370814 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:11]=[CH:10][C:8](=[O:9])O[CH:6]=1)=[O:4].[NH2:12][CH2:13][C@H:14]([OH:16])[CH3:15]>CO>[OH:16][C@H:14]([CH3:15])[CH2:13][N:12]1[C:8](=[O:9])[CH:10]=[CH:11][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6]1

Participants

4

Reactant 2

HCID 80113Methyl coumalateHCID 439938(2R)-1-aminopropan-2-ol

Product 1

HCID 71165424(R)-methyl 1-(2-hydroxypropyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A solution of methyl coumalate (500 mg, 3.24 mmol) in MeOH (10 mL) was treated with (R)-(−)-1-amino-2-propanol (0.319 mL, 4.06 mmol) and TEA (0.790 mL, 5.68 mmol). The reaction was stirred at 23° C. under nitrogen. After 1 h, the reaction was concentrated and purified by silica gel chromatography (eluent: 55-95% EtOAc/hexane), affording (R)-methyl 1-(2-hydroxypropyl)-6-oxo-1,6-dihydropyridine-3-carboxylate as a white solid. MS (ESI pos. ion) m/z: 212.1 (M+1).

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by silica gel chromatography (eluent: 55-95% EtOAc/hexane)

Sources & evidence

ORD record
ord-e9e3c3745ef240a6a32a5b119cbf7032
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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