2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)ethanenitrile

Base Information

• Chemical Name: 2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)ethanenitrile
• CAS No.: 903518-00-3
• Molecular Formula: C₁₅H₁₄N₂O₂
• Molecular Weight: 254.288

Synonyms:2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)ethanenitrile

Chemical Property of 2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)ethanenitrile

Chemical Property:

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Technology Process of 2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)ethanenitrile

There total 3 articles about 2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)ethanenitrile 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: 84.0%

((1S,2S,3S,4S,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.02,4]non-3-yl)methyl methylsulfonate (903517-98-6) + potassium cyanide (151-50-8) → 2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.02,4]non-3-yl)ethanenitrile (903518-00-3)

Guidance literature:

With tetra-n-butylammonium cyanide; In dichloromethane; water; at 20 ℃; for 72h;

DOI:10.1021/jo060210f

Reference yield:

(1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.02,4]nonan-5-one (903517-94-2) → 2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.02,4]non-3-yl)ethanenitrile (903518-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / DMAP / CH₂Cl₂ / 4.5 h / 0 - 20 °C

2: 84 percent / (Bu₄N)CN / CH₂Cl₂; H₂O / 72 h / 20 °C

With dmap; tetra-n-butylammonium cyanide; In dichloromethane; water;

DOI:10.1021/jo060210f

Reference yield:

(1S,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester (220623-03-0) → 2-((1S,2S,3S,4R,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.02,4]non-3-yl)ethanenitrile (903518-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / LiEt₃BH / tetrahydrofuran / 0.5 h / -78 °C

2: 70 percent / DMAP / CH₂Cl₂ / 4.5 h / 0 - 20 °C

3: 84 percent / (Bu₄N)CN / CH₂Cl₂; H₂O / 72 h / 20 °C

With dmap; tetra-n-butylammonium cyanide; lithium triethylborohydride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo060210f

upstream raw materials:

((1S,2S,3S,4S,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)methyl methylsulfonate

potassium cyanide

(1S,2S,3S,4R,7R)-6-aza-3-(hydroxymethyl)-8-oxa-7-phenyltricyclo[4.3.0.0^2,4]nonan-5-one

(1S,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester

Downstream raw materials:

[2-((1S,2S,5R,6R)-3-Benzyl-2-hydroxymethyl-3-aza-bicyclo[3.1.0]hex-6-yl)-ethyl]-carbamic acid tert-butyl ester

[(1S,2S,5R,6R)-6-(2-aminoethyl)-3-aza-3-benzylbicyclo[3.1.0]hex-2-yl]methanol

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