81102-69-4Relevant articles and documents
Practical Syntheses of - and -1-Alkylamino-3-aryloxy-2-porpanols from a Single Carbohydrate Precursor
Tsuda, Yoshisuke,Yoshimoto, Kimihiro,Nishikawa, Terumi
, p. 3593 - 3600 (2007/10/02)
A practical synthetic route to optically active - and -1-alkylamino-3-aryloxy-2-propanols (β-blockers) from -2,3-O-isopropylideneglyceraldehyde (-1) was developed.Synthesis of the -isomers was carried out as follows.Borohydride reduction of -1 in the presence of excess alkylamine followed by alkoxycarbonylation, acid hydrolysis, and cyclization under K2CO3 catalysis gave -3-alkyl-5-hydroxymethyl-1,3-oxazolidin-2-ones, the tosylates of which were coupled with various phenols then hydrolyzed by alkali treatment to give -(-)-β-blockers (e.g., propranolol, carteolol) in satisfactory yields. -,-, and rac-pindolol were synthesized from the corresponding 3-isopropyl-5-(2-methyl-3-nitrophenoxymethyl)-1,3-oxazolidin-2-one by application of the Leimgruber-Batcho method.Keywords--- and -1-alkylamino-3-aryloxy-2-propanols; optically active β-blockers; propranolol; carteolol; pindolol; carbohydrate precursor; -2,3-O-isopropylideneglyceraldehyde; -3-alkyl-5-hydroxymethyl-1,3-oxazolidin-2-ones; Leimgruber-Batcho indole synthesis