2-(N-(3-hydroxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan

Base Information

• Chemical Name: 2-(N-(3-hydroxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan
• CAS No.: 1271174-09-4
• Molecular Formula: C₂₈H₃₃N₃OS
• Molecular Weight: 459.656
• Mol file: 1271174-09-4.mol

Synonyms:2-(N-(3-hydroxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan

Chemical Property of 2-(N-(3-hydroxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(N-(3-hydroxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan

There total 8 articles about 2-(N-(3-hydroxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan 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: 74.0%

2-(N-(3-methoxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan dihydrochloride → 2-(N-(3-hydroxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan (1271174-09-4)

Guidance literature:

2-(N-(3-methoxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan dihydrochloride; With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 3.5h;

With methanol; In dichloromethane; at 20 ℃;

DOI:10.1021/jm101542c

Reference yield:

norlevorphanol (1531-12-0) → 2-(N-(3-hydroxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan (1271174-09-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N,N-dimethyl-formamide / 90 - 95 °C / basic conditions

2.1: triethylamine / dichloromethane / 0 - 20 °C

3.1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tetrahydrofuran / Inert atmosphere; Reflux

4.1: hydroxylamine hydrochloride; sodium acetate / methanol / 36 h / 20 °C

5.1: bromine; acetic acid / 48 h

6.1: toluene-4-sulfonic acid / toluene / 18 h / Reflux

7.1: sodium tetrahydroborate / methanol / 6 h / Reflux

8.1: boron tribromide / dichloromethane / 3.5 h / 0 - 20 °C

8.2: 20 °C

With sodium tetrahydroborate; hydroxylamine hydrochloride; bromine; sodium acetate; palladium diacetate; boron tribromide; caesium carbonate; toluene-4-sulfonic acid; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm101542c

Reference yield:

C29H33N3OS → 2-(N-(3-hydroxybenzyl)amino)thiazolo[5,4-b]-N-(cyclopropylmethyl)morphinan (1271174-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate / methanol / 6 h / Reflux

2.1: boron tribromide / dichloromethane / 3.5 h / 0 - 20 °C

2.2: 20 °C

With sodium tetrahydroborate; boron tribromide; In methanol; dichloromethane;

DOI:10.1021/jm101542c

upstream raw materials:

cyclorphan

norlevorphanol

(-)-3-trifluoromethanesulfonyloxy-N-cyclopropylmethylmorphinan

MCL 149

Refernces