Pyridine → 5-(Methoxy-methylamino)-3-methyl-5-oxopentanoic acid

HRID 1891989Notes

Reaction equation

HRID 1891989 reaction equation
[CH3:1][CH:2]1[CH2:8][C:7](=[O:9])[O:6][C:4](=[O:5])[CH2:3]1.Cl.[CH3:11][NH:12][O:13][CH3:14].N1C=CC=CC=1>ClCCl>[CH3:14][O:13][N:12]([CH3:11])[C:7](=[O:9])[CH2:8][CH:2]([CH3:1])[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 778283-Methylglutaric anhydrideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 140188575-(Methoxy-methylamino)-3-methyl-5-oxopentanoic acidYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methylglutaric anhydride (5.0 g) and N,O-dimethylhydroxylamine hydrochloride (4.19 g) in dichloromethane (100 mL) was stirred at 0° C. and treated dropwise with pyridine (6.9 mL). The resulting solution was warmed to rt over 45 min and then stirred overnight. After this time, the mixture was concentrated under vacuum, and the resulting residue was taken up in saturated aqueous sodium chloride and 1:1 ether/dichloromethane. The aqueous and organic layers were separated and the aqueous layer was extracted three times with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated under vacuum to provide 5-(methoxy(methyl)amino)-3-methyl-5-oxopentanoic acid as a yellow oil (7.27 g). Mass spectrum m/z 188.10 (M−H−).

Workup

  1. concentrationAfter this time, the mixture was concentrated under vacuum
  2. customThe aqueous and organic layers were separated
  3. extractionthe aqueous layer was extracted three times with dichloromethane
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-20585c836ad845f49955d44086157a7b
Source dataset
uspto-grants-2013_08
Patent number
US08507559B2

Reaction notes

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