2-Naphthylamine → N-(2-naphthyl)alanine Methyl Ester

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:12]([O:17][CH3:18])(=[O:16])[C:13]([CH3:15])=O>>[CH3:18][O:17][C:12](=[O:16])[C@H:13]([CH3:15])[NH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1

Participants

Reactant 2

HCID 70572-Naphthylamine

HCID 11748Methyl pyruvate

Product 1

HCID 22876174N-(2-naphthyl)alanine Methyl Ester

Procedure

Following reductive amination General Procedure AA above and using 2-aminonaphthalene (Aldrich) and methyl pyruvate (Aldrich), the title compound was prepared. The reaction was monitored by silica gel tlc (Rf=0.50 in 25% EtOAc/hexanes). Purification was by flash chromatography with silica gel using 25% EtOAc/hexanes as the eluant.

Workup

customPurification

Sources & evidence

ORD record: ord-427cba692fe547f3a607f10f89acd3d0
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849650B2

Reaction notes

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