(2S,6S)-(+)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride

Base Information

• Chemical Name: (2S,6S)-(+)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride
• CAS No.: 1430202-70-2
• Molecular Formula: C₁₂H₁₄ClNO₂*ClH
• Molecular Weight: 276.163
• Mol file: 1430202-70-2.mol

Synonyms:(2S,6S)-(+)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride

Chemical Property of (2S,6S)-(+)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride

Chemical Property:

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,6S)-Hydroxynorketamine hydrochloride ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6S)-(+)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride

There total 5 articles about (2S,6S)-(+)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride 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:

tert-butyl ((1S,3S)-1-(2-chlorophenyl)-3-hydroxy-2-oxocyclohexyl)carbamate → (2S,6S)-(+)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride (1430202-70-2)

Guidance literature:

tert-butyl ((1S,3S)-1-(2-chlorophenyl)-3-hydroxy-2-oxocyclohexyl)carbamate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

With hydrogenchloride; In 1,4-dioxane; ethyl acetate; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02498

Reference yield:

1-<(2-Chlorophenyl)iminomethyl>cyclopentanol hydrochloride (79499-58-4) → (2S,6S)-(+)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride (1430202-70-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium carbonate / diphenylether / 170 - 185 °C / pH 8 - 9 / Large scale

2.1: D-tartaric acid / ethanol / 18 h / Reflux

3.1: benzene / toluene / 16 h / 80 °C

4.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 1 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 °C

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / -15 - 20 °C / Inert atmosphere

5.2: 0.03 h / -5 °C

6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With D-tartaric acid; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; benzene; In tetrahydrofuran; diphenylether; ethanol; n-heptane; dichloromethane; ethylbenzene; toluene;

Reference yield:

norketamine (35211-10-0,83777-65-5) → (2S,6S)-(+)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexanone hydrochloride (1430202-70-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: D-tartaric acid / ethanol / 18 h / Reflux

2.1: benzene / toluene / 16 h / 80 °C

3.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 1 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / -15 - 20 °C / Inert atmosphere

4.2: 0.03 h / -5 °C

5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With D-tartaric acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; benzene; In tetrahydrofuran; ethanol; n-heptane; dichloromethane; ethylbenzene; toluene;

upstream raw materials:

1-<(2-Chlorophenyl)iminomethyl>cyclopentanol hydrochloride

norketamine

(S)-Norketamine

Refernces

• 1、 Han, Yixin,Reddy, Karla Mahender,Corey. "Simple enantioselective syntheses of (2R,6R)-hydroxynorketamine and related potential rapid-onset antidepressants". supporting information. p. 5224 - 5227. Retrieved 2017/11/06.