1316259-32-1

Basic information

• Product Name: (R)-1-(3-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: (R)-1-(3-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 1316259-32-1
• Molecular Weight: 253.344
• Mol File: 1316259-32-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-1-(3-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(3-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline(1316259-32-1)
• EPA Substance Registry System: (R)-1-(3-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline(1316259-32-1)

Safety Data

• Hazardous Substances Data: 1316259-32-1(Hazardous Substances Data)

Upstream product

• 1316259-07-0 1-(3-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 138350-92-2 tert-butyl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate 
• 1700-30-7 (3-(benzyloxy)phenyl)methanol 
• 1700-31-8 3-benzyloxybenzyl bromide 
• 1316258-70-4 1-(3-benzyloxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1316258-68-0 tert-butyl 1-(3-benzyloxybenzyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion

Deracemization, that is, the transformation of a racemate into a single product enantiomer with theoretically 100-% conversion and 100-% ee, is an appealing but also challenging option for asymmetric synthesis. Herein a novel chemo-enzymatic deracemization concept by a cascade is described: the pathway involves two enantioselective oxidation steps and one non-stereoselective reduction step, enabling stereoinversion and a simultaneous kinetic resolution. The concept was exemplified for the transformation of rac-benzylisoquinolines to optically pure (S)-berbines. The racemic substrates were transformed to optically pure products (ee>97-%) with up to 98-% conversion and up to 88-% yield of isolated product. From two make one: Chemo-enzymatic stereoinversion and enzymatic kinetic resolution have been combined in a simultaneous cascade process to transform racemic substrates (A, ent-A) into optically pure product P. The concept was exemplified for benzylisoquinolines rac-1 yielding optically pure berbines (S)-2. The reaction system comprised a monoamine oxidase (MAO-N), morpholine-borane, and the berberine bridge enzyme (BBE).

Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids

A chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative C-C bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine, a sedative and muscle relaxing agent. The racemic substrates rac-1 required for the biotransformation were prepared in 4-8 linear steps using either a Bischler-Napieralski cyclization or a C1-Cα alkylation approach. The chemoenzymatic synthesis was applied to the preparation of fourteen enantiomerically pure alkaloids, including the natural products (S)-scoulerine and (R)-reticuline, and gave overall yields of up to 20% over 5-9 linear steps.