Hydroxylamine → Dopamine

Participants

Reaction Steps

(1S)-(-)-α-pinene, 6-nitropiperonal, boron tribromide, glycine ethyl ester, lithium aluminum hydride (1M in diethyl ether) and thionyl bromide were obtained from Aldrich. Glycine t-butyl ester was purchased from Sigma Chemical Company. Hydroxylamine (free base) was obtained from Southwestern Analytic Chemicals, Inc. 6-Fluoronorepinephrine was purchased from RBI (Research Biochemicals Inc.). Dopamine and dopamine β-hydroxylase was obtained from the Sigma Chemical Co. 1H NMR spectra were also recorded with a Brucker 300 MHz in CDCl3 as a solvent using TMS as internal reference. Mass spectra were recorded with a Finnegan-Mat GC-MS 5100 mass spectrometer using electron impact ionization at 70 eV. HPLC analyses were carried out with a Perkin-Elmer liquid chromatograph equipped with a radioactivity monitor and UV detector. Optical rotation analysis was performed by Rudolph Instruments, Inc.

Provenance & Evidence