(2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol

Base Information

• Chemical Name: (2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol
• CAS No.: 1231951-92-0
• Molecular Formula: C₁₄H₂₀ClNO₂
• Molecular Weight: 269.771
• Mol file: 1231951-92-0.mol

Synonyms:(2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol

Chemical Property of (2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol

There total 4 articles about (2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol 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: 63.0%

radafaxine (192374-14-4,233600-52-7) + methyl iodide (74-88-4) → (2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol (1231951-92-0)

Guidance literature:

radafaxine; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; at 70 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jm1003232

Reference yield:

(Z)-tert-butyl-[1-(3-chlorophenyl)prop-1-enyloxy]dimethylsilane (291275-45-1) → (2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol (1231951-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,4-bis(9-O-dihydroquinidine)phthalazine; methanesulfonamide / water; tert-butyl alcohol / 16 h / 0 °C

2.1: trifluoromethylsulfonic anhydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 1 h / -50 - 0 °C

2.2: 4 h / -10 - 0 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere

3.2: 24 h / 70 °C / Inert atmosphere

With methanesulfonamide; trifluoromethylsulfonic anhydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

Reference yield:

3'-chloro-propiophenone (34841-35-5) → (2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol (1231951-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 20 °C / Cooling with ice

2.1: 1,4-bis(9-O-dihydroquinidine)phthalazine; methanesulfonamide / water; tert-butyl alcohol / 16 h / 0 °C

3.1: trifluoromethylsulfonic anhydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 1 h / -50 - 0 °C

3.2: 4 h / -10 - 0 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere

4.2: 24 h / 70 °C / Inert atmosphere

With methanesulfonamide; trifluoromethylsulfonic anhydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

upstream raw materials:

radafaxine

methyl iodide

3'-chloro-propiophenone

(R)-(+)-1-(3-chlorophenyl)-2-hydroxypropan-1-one