(S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine

Base Information

• Chemical Name: (S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine
• CAS No.: 1425458-23-6
• Molecular Formula: C₃₁H₃₆ClN₃O₂S
• Molecular Weight: 550.165

Synonyms:(S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine

Chemical Property of (S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine

Chemical Property:

Purity/Quality:

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Technology Process of (S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine

There total 2 articles about (S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine 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: 71.0%

(SS)-α-chloro-N-p-toluenesulfinyl isobutyraldimine (1365547-75-6) + N-(diphenylmethylene)-2-oxo-2-(piperidin-1-yl)ethanamine → (SS,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine (1425458-23-6)

Guidance literature:

N-(diphenylmethylene)-2-oxo-2-(piperidin-1-yl)ethanamine; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

(S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine; In tetrahydrofuran; at -78 ℃; for 0.25h; diastereoselective reaction; Inert atmosphere;

DOI:10.3762/bjoc.8.239

Reference yield:

(S)-p-toluenesulfinimide (188447-91-8) → (SS,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine (1425458-23-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: titanium(IV) tetraethanolate / dichloromethane / 18 h / 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 0.25 h / -78 °C / Inert atmosphere

With titanium(IV) tetraethanolate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.3762/bjoc.8.239

Reference yield: 90.0%

(SS,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine (1425458-23-6) → (SS,2S,2'S)-N-{2-(diphenylmethyleneamino)-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetyl}piperidine (1425458-35-0)

Guidance literature:

With potassium carbonate; In acetone; for 24h; Reflux;

DOI:10.3762/bjoc.8.239

upstream raw materials:

(S)-p-toluenesulfinimide

(S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine

Downstream raw materials:

(S_S,2S,2'S)-N-{2-(diphenylmethyleneamino)-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetyl}piperidine

(S_S,2S,2'S)-N-{2-amino-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetyl}piperidine

(4'S,5'S)-N-[5-(2-chloro-2-propyl)-2,2-diphenylimidazolidin-4-yl]carbonylpiperidine

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