methyl (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylate

Base Information

• Chemical Name: methyl (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylate
• CAS No.: 149343-50-0
• Molecular Formula: C₂₆H₃₁NO₃
• Molecular Weight: 405.537

Synonyms:methyl (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylate

Chemical Property of methyl (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylate

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Technology Process of methyl (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylate

There total 1 articles about methyl (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

(2R,6R,11R)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol (16603-67-1) + methyl (-)-(1S,2R)-2-(bromomethyl)-1-phenylcyclopropanecarboxylate (290341-76-3) → methyl (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylate (149343-50-0)

Guidance literature:

With sodium hydrogencarbonate; potassium iodide; In butanone; at 60 ℃; for 18h;

DOI:10.1691/ph.2007.11.7523

Reference yield: 91.0%

methyl (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylate (149343-50-0) → (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylic acid (149343-48-6)

Guidance literature:

With sodium hydroxide; In water; for 5h; Reflux;

DOI:10.1691/ph.2007.11.7523

Reference yield: 23.0%

methyl (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylate (149343-50-0) + methylamine (74-89-5) → (-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-N-methyl-1-phenylcyclopropanecarboxamide (1001017-69-1)

Guidance literature:

In methanol; water; at 70 ℃; for 48h;

DOI:10.1691/ph.2007.11.7523

upstream raw materials:

(2R,6R,11R)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol

methyl (-)-(1S,2R)-2-(bromomethyl)-1-phenylcyclopropanecarboxylate

Downstream raw materials:

(-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxylic acid

(-)-(1S,2R)-N-ethyl-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-1-phenylcyclopropanecarboxamide

(-)-(1S,2R)-2-{[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]methyl}-N-methyl-1-phenylcyclopropanecarboxamide

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