Trimethylsilyl cyanide → 4-(2-Aminoethyl)-5-fluorobenzene-1,2-diol

HRID 1656852Notes

Reaction equation

HRID 1656852 reaction equation
[Si](C#N)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:13]1[C:18]([OH:19])=[C:17]([OH:20])[CH:16]=[C:15]([F:21])[C:14]=1[CH:22](O)[CH2:23][NH2:24].Cl>>[F:21][C:15]1[C:14]([CH2:22][CH2:23][NH2:24])=[CH:13][C:18]([OH:19])=[C:17]([OH:20])[CH:16]=1

Participants

4

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 119574796-Fluoronorepinephrine hydrochlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 1222374-(2-Aminoethyl)-5-fluorobenzene-1,2-diol

Procedure

FIG. 6 shows HPLC traces of a reaction mixture resulting from the incubation of dopamine with dopamine β-hydroxylase; (a) reaction at 1 min; (b) reaction at 1 h; and (c) coinjection of b with racemic NE. In less than 1 hour, a peak corresponding to (-)-NE (retention time 6.7 minutes) appeared when the enzyme mixture which contained dopamine as substrate was injected onto a chiral HPLC column; (+)-NE was not observed (FIG. 6). FIG. 7 shows HPLC traces of a reaction mixture resulting from the incubation of 6-fluorodopamine with dopamine β-hydroxylase: (a) reaction at 2 min; (b) reaction at 1 h; and (c) coinjection of b with racemic 6-FNE. An analogous result was obtained when 6-fluorodopamine was used as a substrate; a new HPLC peak at 18 minutes appeared (FIG. 7). Thus UV peak coeluted with the first radioactive peak collected from 6-[18F]FNE. Thus the levorotatory isomers of both NE and 6-FNE elute before their respective dextrorotatory enantiomers. This order of elution was also recently reported by Maeda et al., Appl. Radiat. Isot., 41, 463 (1990) the disclosure of which is incorporated by reference herein, for [11C]octopamine enantiomers when a Crownpak CR(+) HPLC column was used.

Workup

  1. customAn analogous result

Sources & evidence

ORD record
ord-8e90ab368095459f95051ca1b7c7a3f9
Source dataset
uspto-grants-1993_10
Patent number
US05254726

Reaction notes

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