36770-70-4

Upstream product

• 156896-96-7 (4S)-(+)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutene 
• 255721-20-1 (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutyl acetate 
• 255721-21-2 (4S)-(-)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl acetate 
• 255721-22-3 (4R)-(+)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl acetate 
• 349078-89-3 (4E,3R)-(-)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enol 
• 349078-90-6 (4E,3S)-(+)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enol 
• 349078-83-7 Acetic acid (Z)-(S)-3-(3,4-dimethoxy-phenyl)-1,4-dimethyl-pent-2-enyl ester 
• 349078-78-0 Acetic acid (Z)-(R)-3-(3,4-dimethoxy-phenyl)-1,4-dimethyl-pent-2-enyl ester 
• 349078-84-8 (E,R)-(-)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enoic acid 
• 349078-85-9 (E,S)-(+)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enoic acid 
• 349078-87-1 methyl (4E,3R)-(-)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enoate 
• 349078-88-2 methyl (4E,3S)-(+)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enoate 
• 349078-93-9 (5E,4R)-(-)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-enenitrile 
• 349078-94-0 (5E,4S)-(+)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-enenitrile 

Downstream Products

• 107241-84-9 (S)-4-(3,4-Dimethoxy-phenyl)-N¹-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-isopropyl-N¹-methyl-pentane-1,5-diamine 
• 107241-85-0 (R)-4-(3,4-Dimethoxy-phenyl)-N¹-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-isopropyl-N¹-methyl-pentane-1,5-diamine 
• 107149-06-4 N-<(2R)-2-(3,4-dimethoxyphenyl)-2-isopropyl-5-<(3,4-dimethoxyphenethyl)methylamino>pentyl>-(1S)-10-camphorsulfonamide 
• 107149-06-4 N-<(2S)-2-(3,4-dimethoxyphenyl)-2-isopropyl-5-<(3,4-dimethoxyphenethyl)methylamino>pentyl>-(1S)-10-camphorsulfonamide 
• 36622-29-4 (S)-verapamil 
• 255721-21-2 (4S)-(-)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl acetate 
• 255721-20-1 (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutyl acetate 
• 251317-75-6 N¹-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-1,5-pentanediamine 
• 251317-77-8 N¹-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-N⁵-methyl-1,5-pentanediamine 
• 251317-76-7 2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-1,5-pentanediamine 
• 251317-78-9 2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-N⁵-methyl-1,5-pentanediamine 
• 251317-74-5 1-[5-(t-butoxycarbonyl)amino-4-(3,4-dimethoxyphenyl)-4-isopropyl-1-pentyl] methanesulfonate 
• 251317-73-4 5-(t-butoxycarbonyl)amino-4-(3,4-dimethoxyphenyl)-4-isopropyl-1-pentanol 
• 36622-23-8 4-cyano-4-(3,4-dimethoxyphenyl)-5-methyl hexanoic acid 

Relevant academic research and scientific papers

Synthesis of the Verapamil Intermediate through the Quaternary Carbon-Constructing Allylic Substitution

In the present study, the key secondary allylic picolinate was synthesized via Pd(PPh 3) 4 -catalyzed coupling of the TBS ether of (R, Z)-4-iodo-5-methylhex-3-en-2-ol with allyl-MgBr. Allylic substitution of the picolinate with the copper reagent derived from 3,4-(MeO) 2 C 6 H 3 MgBr and Cu(acac) 2 in a 2:1 ratio afforded the anti S N 2′ product with complete chirality transfer and 91% regioselectivity. Synthetic manipulation of the olefin moiety led to the nitrile group, generating the intermediate for the synthesis of (S)-verapamil.

Enzyme-mediated synthesis of (S)- And (R)-verapamil

A lipase-mediated synthesis of (S)- And (R)-verapamil is described. The key steps of the synthetic sequence are the enantioselective acetylation, mediated by Lipase PS, of allylic alcohol (Z)-(±)-2, affording the acetate derivative (Z,R)-(-)-3 (ee 92%) and the Ireland-Claisen rearrangement of this latter and of its enantiomer (Z,S)-(+)-3 (ee 92%) to afford acid derivatives (E,R)-(-)-4 (ee 94%) and (E,S)-(+)-4 (ee 93%), precursors of (S)- and (R)-verapamil, respectively.

Enzyme-catalysed improved resolution of (RS)-4-cyano-4-(3,4- dimethoxyphenyl)-4-isopropyl-1-butanol

Resolutions of (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropyl-1- butanol 1 using various enzymes were performed. Among them, Pseudomonas fluorescens resolved it with moderate stereoselectivity (E=13) and reacted faster with the (S)-enantiomer. To optimize enzyme-catalysed reaction conditions for the resolution, the effect of solvents and additives was studied. In n-hexane:ethyl acetate (9:1), both reaction rate and selectivity were high. When pyridine, potassium carbonate and molecular sieves were used as additives, the enantiomeric excess of the (R)-enantiomer was 99, 99 and 98% at 52-60% conversion, respectively. However, in diisopropyl ether, the enantiomeric excess of unreacted alcohol (R)-1 was up to 99% at 70% conversion without additives.

Synthesis and binding properties of photoactivable biotin-conjugated verapamil derivatives for the study of P-170 glycoprotein

The design and synthesis of two photoactivable biotin-labeled analogues of verapamil (6 and 7) is reported. Preliminary evaluation of the biological profile of 6 (EDP 137) and 7 (EDP 141) shows that they have comparable affinities to that of verapamil for