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

Base Information

• Chemical Name: (S_S,2S,2'S)-N-{2-amino-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetyl}piperidine
• CAS No.: 1425458-49-6
• Molecular Formula: C₁₈H₂₇N₃O₂S
• Molecular Weight: 349.497

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

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

Chemical Property:

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

There total 3 articles about (S_S,2S,2'S)-N-{2-amino-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetyl}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: 86.0%

(SS,2S,3S)-N-[2-amino-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine → (SS,2S,2'S)-N-{2-amino-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetyl}piperidine (1425458-49-6)

Guidance literature:

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

DOI:10.3762/bjoc.8.239

Reference yield:

(SS,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]piperidine (1425458-23-6) → (SS,2S,2'S)-N-{2-amino-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetyl}piperidine (1425458-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / acetone; water / 0.25 h / 20 °C

2: potassium carbonate / acetone / 24 h / Reflux

With potassium carbonate; trifluoroacetic acid; In water; acetone;

DOI:10.3762/bjoc.8.239

Reference yield:

(SS)-α-chloro-N-p-toluenesulfinyl isobutyraldimine (1365547-75-6) → (SS,2S,2'S)-N-{2-amino-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetyl}piperidine (1425458-49-6)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 0.25 h / -78 °C / Inert atmosphere

2.1: trifluoroacetic acid / acetone; water / 0.25 h / 20 °C

3.1: potassium carbonate / acetone / 24 h / Reflux

With potassium carbonate; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; water; acetone;

DOI:10.3762/bjoc.8.239

upstream raw materials:

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

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

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