Methyl pyruvate → N-(3,4-methylenedioxyphenyl)alanine Iso-butyl Ester

HRID 411446

Reaction equation

HRID 411446 reaction equation
C1O[C:9]2C=CC(N)=[CH:4][C:3]=2O1.C(OC)(=O)C(C)=O.[CH3:18][O:19][C:20](=[O:33])[C@H:21]([CH3:32])[NH:22][C:23]1[CH:28]=[CH:27][C:26]2[O:29][CH2:30][O:31][C:25]=2[CH:24]=1>C(O)C(C)C>[CH2:18]([O:19][C:20](=[O:33])[C@H:21]([CH3:32])[NH:22][C:23]1[CH:28]=[CH:27][C:26]2[O:29][CH2:30][O:31][C:25]=2[CH:24]=1)[CH:3]([CH3:4])[CH3:9]

Participants

5

Reactant 3

HCID 11748Methyl pyruvateHCID 843101,3-Benzodioxol-5-amineHCID 54531586N-(3,4-methylenedioxyphenyl)alanine methyl ester

Product 1

HCID 54134455N-(3,4-methylenedioxyphenyl)alanine Iso-butyl Ester

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

Following reductive amination General Procedure AA above and using 3,4-methylenedioxyaniline (Aldrich) and methyl pyruvate (Aldrich), N-(3,4-methylenedioxyphenyl)alanine methyl ester was prepared. The methyl ester was then transesterified following General Procedure AQ above and using iso-butanol to provide the title compound as an oil. The reaction was monitored by silica gel tlc (Rf=0.61 in 25% EtOAc/hexanes). Purification was by preparative plate chromatography with silica gel using 25% EtOAc/hexanes as the eluant.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-9e8ba79135094acdb0bbd1b211c52528
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Linked notes

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