A new synthesis of β-amino alcohols

✍ Scribed by William E. Parham; Christopher S. Roosevelt

• Book ID: 104247518
• Publisher: Elsevier Science
• Year: 1971
• Tongue: French
• Weight: 181 KB
• Volume: 12
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)96590-6

✦ Synopsis

The usual pathwsys' for preparing ~-amino alcohols for use in the Tiffeneau-Demjanov reaction involve either preparation of cyanohydrins or t3-nitroalcohols fYan ketones, followed by reduction. Difficulty is encountered with some conjugated and sterically hindered ketones with the initisl addition reaction. Recently we have described the synthesis of ,%amino ethers from ketones for use in a modified Tiffeneau-Mnjanov reaction,2 and now wish to report a new synthetic procedure for B-amino alcohols.

Preliminary work was done with the cyclohexsne system. Cyclohexsnone was converted to the l known trimethylsilyl enol ether & by alternate procedures reported by House3 and by Stork.'+ Addition of & to excess, liquid, anhydrous hydrogen cyanide containing a drop of sulfuric acid (four hours at O", then twelve hours at 20°) yielded 49% a-cyanocyclohexyl trimethylsilyl ether 2 as a clear, colorless oil [bp13 102-105°; ir (neat): u 2210 w (-EN), v 1247 s, 836 s, 742 m (-I-CH3);