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

HRID 133340

Reaction equation

HRID 133340 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 dc (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-12e04e799171427d96503c1f1f1c2440
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Linked notes

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