147624-55-3

Upstream product

• 645-36-3 2,2-diethoxy-ethanamine 
• 147624-54-2 (benzyloxy)methyl-3,4-dimethoxyphenyl ketone 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 1448706-86-2 N-(2,2-diethoxyethyl)-2-(3,4-dimethoxyphenyl)glycinol 
• 100-39-0 benzyl bromide 
• 1448706-79-3 N-benzyl-N-(2,2-diethoxyethyl)-2-(3,4-dimethoxyphenyl)glycinol 
• 61190-10-1 N-benzyl-N-(2,2-diethoxyethyl)amine 
• 147624-53-1 1-(3,4-dimethoxyphenyl)-2-(benzyloxy)ethanol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 140687-75-8 2-(3,4-dimethoxyphenyl)oxirane 

Downstream Products

• 94914-96-2 1-benzyloxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline; hydrochloride 
• 486-99-7 (6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinolyl)methanol 

Relevant academic research and scientific papers

Synthesis of calycotomine and N-methylcalycotomine using a petasis reaction-pomeranz-fritsch-bobbitt cyclization sequence

The use of aminoacetaldehyde acetals as the amine components in the one-step, three-component Petasis reaction followed by the Pomeranz-Fritsch- Bobbitt cyclization has been shown to be a convenient and simple method for the synthesis of tetrahydroisoquinoline alkaloids. Using this method two alkaloids, calycotomine and N-methylcalycotomine hydrochlorides, have been prepared in 61% overall yield.

Extension of the Bobbitt acetal cyclization to the elaboration of 1-hydroxymethyl-substituted simple tetrahydroisoquinolines. A new synthesis of calycotomine

Aromatic benzyloxymethyl ketones are convenient intermediates for the elaboration, via the Bobbitt acetal cyclization, of 1-hydroxymethyl-substituted simple tetrahydroisoquinolines, such as calycotomine and one bearing the 1,7,8-oxygenated substitution pa