(1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

Base Information

• Chemical Name: (1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one
• CAS No.: 446246-08-8
• Molecular Formula: C₁₈H₂₃NO₂S
• Molecular Weight: 317.452

Synonyms:(1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

Chemical Property of (1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

There total 12 articles about (1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-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: 78.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (1R,2S,6R,7S)-(-)-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (41719-63-5,141117-60-4,141117-61-5,131897-87-5) + thiophenol (108-98-5) → (1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (446246-08-8)

Guidance literature:

formaldehyd; (1R,2S,6R,7S)-(-)-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one; With toluene-4-sulfonic acid; In benzene; at 25 ℃; for 0.5h;

thiophenol; In benzene; for 8h; Heating;

DOI:10.1016/S0957-4166(02)00043-5

Reference yield: 72.0%

phenylthiomethyl chloride (7205-91-6) + (1R,2S,6R,7S)-(-)-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (41719-63-5,141117-60-4,141117-61-5,131897-87-5) → (1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (446246-08-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; for 6h; Heating;

DOI:10.1016/S0957-4166(02)00043-5

Reference yield:

(1R,2S,6R,7S)-(-)-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (41719-63-5,141117-60-4,141117-61-5,131897-87-5) → (1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (446246-08-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 72 percent / sodium hydride; Bu₄NI / tetrahydrofuran / 6 h / Heating

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 °C

2.2: 72 percent / tetrahydrofuran; hexane / 1 h / -100 °C

3.1: 80 percent / mercuric acetate; aqueous acetic acid; calcium carbonate / 80 °C / pH 7

4.1: p-toluenesulfonic acid / benzene / 0.5 h / 25 °C

4.2: 78 percent / benzene / 8 h / Heating

With n-butyllithium; mercury(II) diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; calcium carbonate; In tetrahydrofuran; hexane; benzene; 2.2: Corey-Seebach reaction;

DOI:10.1016/S0957-4166(02)00043-5

upstream raw materials:

phenylthiomethyl chloride

(1R,2S,6R,7S)-(-)-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

formaldehyd

thiophenol

Downstream raw materials:

(1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-2-phenyl-1-(phenylsulfanyl)ethyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

(1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-2-cyclohexyl-1-(phenylsulfanyl)ethyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

(1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

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