(S_S,3S)-(+)-8-chloro-4-[N-(p-toluenesulfinyl)amino]octan-2-one

Base Information

• Chemical Name: (S_S,3S)-(+)-8-chloro-4-[N-(p-toluenesulfinyl)amino]octan-2-one
• CAS No.: 507453-98-7
• Molecular Formula: C₁₅H₂₂ClNO₂S
• Molecular Weight: 315.864
• Mol file: 507453-98-7.mol

Synonyms:(S_S,3S)-(+)-8-chloro-4-[N-(p-toluenesulfinyl)amino]octan-2-one

Chemical Property of (S_S,3S)-(+)-8-chloro-4-[N-(p-toluenesulfinyl)amino]octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S_S,3S)-(+)-8-chloro-4-[N-(p-toluenesulfinyl)amino]octan-2-one

There total 4 articles about (S_S,3S)-(+)-8-chloro-4-[N-(p-toluenesulfinyl)amino]octan-2-one 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: 77.0%

methylmagnesium bromide (75-16-1) + (SS,3S)-(+)-7-chloro-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methylheptanamide (507453-97-6) → (SS,3S)-(+)-8-chloro-4-[N-(p-toluenesulfinyl)amino]octan-2-one (507453-98-7)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 2h;

DOI:10.1021/ol034119z

Reference yield:

(S)-(+)-N-(5-chloropentylidene)-p-toluenesulfinamide (507453-96-5) → (SS,3S)-(+)-8-chloro-4-[N-(p-toluenesulfinyl)amino]octan-2-one (507453-98-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / KHMDS / toluene; diethyl ether / 2 h / -78 °C

2: 77 percent / tetrahydrofuran / 0.5 h / -78 - 20 °C

With potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1021/jo0402780

Reference yield:

5-chloro-pentanal (20074-80-0) → (SS,3S)-(+)-8-chloro-4-[N-(p-toluenesulfinyl)amino]octan-2-one (507453-98-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 54 percent / Ti(OEt)4 / CH₂Cl₂ / 1 h / 20 °C

2.1: KHMDS / tetrahydrofuran; toluene / 0.75 h / -78 °C

2.2: 76 percent / tetrahydrofuran; toluene / 1.5 h / -78 °C

3.1: 77 percent / tetrahydrofuran; diethyl ether / 2 h / -78 - 20 °C

With titanium(IV) tetraethanolate; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 3.1: Grignard reaction;

DOI:10.1021/ol034119z

upstream raw materials:

methylmagnesium bromide

(S_S,3S)-(+)-7-chloro-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methylheptanamide

(S)-(+)-N-(5-chloropentylidene)-p-toluenesulfinamide

5-chloro-pentanal

Downstream raw materials:

(2R)-3-[(S_S,2S)-N-(p-toluenesulfinyl)piperidin-2-yl]propan-2-ol

(2S)-3-[(S_S,2S)-N-(p-toluenesulfinyl)piperidin-2-yl]propan-2-ol

(+)-(2R)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol

(+)-(2S)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol