Ethyl Acetate → HCID 72189520, compound

HRID 1670729Notes

Reaction equation

HRID 1670729 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.[C:23](=O)([O-])[O-:24].[K+].[K+].C(OCC)(=O)C>C(O)=O>[CH:23]([NH:1][CH2:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)=[O:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67350745HCID 67350745, compound

Product 1

HCID 72189520HCID 72189520, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methyl 3-(6-(aminomethyl)pyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (0.24 g, 0.80 mmol) in formic acid (3 mL) was added potassium carbonate (0.2 g) portionwise. The reaction mixture was stirred at 90° C. overnight under argon and then concentrated. The residue was made basic with saturated aqueous sodium bicarbonate solution (20 mL) and extracted with dichloromethane (3×20 mL). The combined dichloromethane extracts were dried (Na2SO4) and concentrated. Silica gel flash chromatography (20-100% ethyl acetate in hexanes) gave methyl 3-(6-(formamidomethyl)pyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (0.19 g, 0.58 mmol, 73% yield) as a solid. MS found: (M+H)+=327.35.

Workup

  1. concentrationconcentrated
  2. extractionextracted with dichloromethane (3×20 mL)
  3. dry with materialThe combined dichloromethane extracts were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c48d2a0fe1f0459da8d578013b5728ff
Source dataset
uspto-grants-2011_08
Patent number
US07994190B2

Reaction notes

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