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Regioselective syntheses of deuterium labelled 6-hydroxydopamines

✍ Scribed by John Simmons; Ronald T. Borchardt

Publisher
John Wiley and Sons
Year
1983
Tongue
French
Weight
373 KB
Volume
20
Category
Article
ISSN
0022-2135

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✦ Synopsis

Convenient syntheses of 2,4-,a,a-and 5,B-deuterium labelled 6-hydroxydopamines have been developed. 2,4,5-Trimethoxybenzaldehyde (1) was reductively aminated to give 2,4,5-trimethoxybenzylamine (2). Quaternization of the amine with methyliodide followed by displacement with cyanide gave 2,4,5-trimethoxybenzylcyanide (4). A LiAlD4 reduction of 5 gave a,a-[2H]-B-(2,4,5-trimet~oxy-pheny1)-ethylamine (5). Treatment of benzylcyanide 3 with n-buty lli thium/D20 gave a, a-[ 2H 1a-cyano-2,4,5t r imethoxytoluene (1) which upon reduction afforded B, B-[2H]--B-(2,4,5-trimethoxyphenyl)-ethylamine (8). Treatment of 2,4,5-trimethoxydimeth lbenzylamine 2 with n-butyllithium/D20 gave 3,6-[$HI -2,4,5-trimethoxydimethylbenzylamine (10). The ring deuterium atoms were retained through subsequent steps to afford B-(3,6-[2H]-2,4,5-tri-methoxypheny1)-ethylamine (2). Removal of the phenol protecting groups afforded the deuterium labelled 2,4,5-trihydroxyphenethylamines (6-hydroxydopamines).

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