(5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid

Base Information

• Chemical Name: (5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid
• CAS No.: 156246-77-4
• Molecular Formula: C₂₆H₂₇N₃O₅
• Molecular Weight: 461.517
• Mol file: 156246-77-4.mol

Synonyms:

Chemical Property of (5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid

There total 1 articles about (5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid 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: 33.0%

benzoyl chloride (98-88-4) + <5R-(5α,7β,8β,10β,11β,11aβ)>-7-cyano-5,7,8,9,10,11,11a,12-octahydro-4-methoxy-5-(hydroxymethyl)-13-methyl-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid (96251-59-1) → (5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid (156246-77-4)

Guidance literature:

With pyridine; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)80645-1

Reference yield:

(5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid (156246-77-4) → (5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-10-formyl-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 2 h

2: sodium borohydride / tetrahydrofuran / 1 h / Ambient temperature

3: 1.) dimethyl sulfoxide, oxalyl chloride; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) CH₂Cl₂, -25 deg C, 30 min

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)80645-1

Reference yield:

(5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid (156246-77-4) → (5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-10-hydroxymethyl-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline (156246-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 2 h

2: sodium borohydride / tetrahydrofuran / 1 h / Ambient temperature

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)80645-1

upstream raw materials:

benzoyl chloride

<5R-(5α,7β,8β,10β,11β,11aβ)>-7-cyano-5,7,8,9,10,11,11a,12-octahydro-4-methoxy-5-(hydroxymethyl)-13-methyl-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid

Downstream raw materials:

C₃₀H₃₃N₃O₇

(5R,7R,8S,10R,11R,11aS)-5-benzoyloxymethyl-7-cyano-10-hydroxymethyl-4-methoxy-13-methyl-5,7,8,9,10,11,11a,12-octahydro-8,11-iminoazepino<1,2-b>isoquinoline