Ethanolamine → 1-Aminocyclopentanemethanol

Participants

Reaction Steps

2,3-Dimethylaniline was converted to 2,3-dimethyl-4-iodoaniline according to Method A5a. The aniline was converted to 2,3-dimethyl-4-iodophenyl isothiocyanate according to Method A2a, Step 3. 1-Amino-1-(hydroxymethyl)cyclopentane was synthesized as described in Method B1c. The 2-hydroxyethylamine was reacted with SOCl2 followed by 2,3-dimethyl-4-iodophenyl isothiocyanate according to Method C2a to give 2-(2,3-dimethyl-4-iodophenylimino)-1-thia-3-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give 3-isobutyl-2-(4-iodo-2-n-propylphenylimino)-1-thia-3-azaspiro[4.4]nonane. The phenyl iodide was reacted with trimethylsilylacetylene according to Method D8a, Step 1 to give 3-isobutyl-2-(2,3-dimethyl-4-(2-trimethylsilylethynyl)phenylimino)-1-thia-3-azaspiro[4.4]nonane. The silylacetylene was deprotected according to Method D8a, Step 2 to afford 3-isobutyl-2-(2,3-dimethyl-4-ethynylphenylimino)-1-thia-3-azaspiro[4.4]nonane.

Provenance & Evidence