Tetraethylammonium tetrahydroborate → Methyl 2-(2-hydroxypropan-2-yl)-6-(4-methylphenyl)pyridine-4-carboxylate

HRID 1909128Notes

Reaction equation

HRID 1909128 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[C:10]([C:18]([CH3:20])=[CH2:19])[N:9]=2)=[CH:4][CH:3]=1.[BH4-].C([N+](CC)(CC)CC)C.C([O-])(O)=[O:32].[Na+]>CO.COCCOC.O>[OH:32][C:18]([C:10]1[CH:11]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=1)([CH3:20])[CH3:19]

Participants

7

Reactant 3

HCID 28251Tetraethylammonium tetrahydroborateHCID 516892Sodium BicarbonateHCID 67339741Methyl 2-(4-methylphenyl)-6-(prop-1-en-2-yl)pyridine-4-carboxylate

Product 1

HCID 67339432Methyl 2-(2-hydroxypropan-2-yl)-6-(4-methylphenyl)pyridine-4-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of methyl 2-(4-methylphenyl)-6-(prop-1-en-2-yl)pyridine-4-carboxylate (191 mg, 0.71 mmol) in methanol (3.6 mL) and DME (3.6 mL) was added cobalt(II)mesotetraphenylporphine (2.4 mg, 3.6 mop. After 30 min, tetraethylammonium borohydride (170 mg, 1.17 mmol) was added in 3 portions over 1 h. Saturated aqueous NaHCO3 was added. The mixture was diluted with water and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase chromatography (C-18, 90% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (165 mg). MS 286.1 (M+1).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by reverse phase chromatography (C-18, 90% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-3240b01d78964a7f9c81768f8054afd4
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

Loading…