(1S,2S,6R)-2-(5-aza-7-oxa-4-oxo-6-phenylbicyclo[3.3.0]oct-2-yl)ethanenitrile

Base Information

• Chemical Name: (1S,2S,6R)-2-(5-aza-7-oxa-4-oxo-6-phenylbicyclo[3.3.0]oct-2-yl)ethanenitrile
• CAS No.: 254909-28-9
• Molecular Formula: C₁₄H₁₄N₂O₂
• Molecular Weight: 242.277

Synonyms:(1S,2S,6R)-2-(5-aza-7-oxa-4-oxo-6-phenylbicyclo[3.3.0]oct-2-yl)ethanenitrile

Chemical Property of (1S,2S,6R)-2-(5-aza-7-oxa-4-oxo-6-phenylbicyclo[3.3.0]oct-2-yl)ethanenitrile

Chemical Property:

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Technology Process of (1S,2S,6R)-2-(5-aza-7-oxa-4-oxo-6-phenylbicyclo[3.3.0]oct-2-yl)ethanenitrile

There total 2 articles about (1S,2S,6R)-2-(5-aza-7-oxa-4-oxo-6-phenylbicyclo[3.3.0]oct-2-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: 68.0%

(3R,7S,7aS)-7-Cyanomethyl-5-oxo-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazole-6-carboxylic acid ethyl ester (254909-21-2) → (1S,2S,6R)-2-(5-aza-7-oxa-4-oxo-6-phenylbicyclo[3.3.0]oct-2-yl)ethanenitrile (254909-28-9)

Guidance literature:

With bis(tri-n-butyltin)oxide; In toluene; for 16h; Heating;

DOI:10.1039/a906297a

Reference yield: 68.0%

(2R,5S,6S,7S)-7-ethyloxycarbonyl-6-cyanomethyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane (864381-91-9) → (1S,2S,6R)-2-(5-aza-7-oxa-4-oxo-6-phenylbicyclo[3.3.0]oct-2-yl)ethanenitrile (254909-28-9)

Guidance literature:

With bis(tri-n-butyltin)oxide; In toluene; for 17h; Heating;

DOI:10.1039/b503994k

Reference yield: 75.0%

(1S,2S,6R)-2-(5-aza-7-oxa-4-oxo-6-phenylbicyclo[3.3.0]oct-2-yl)ethanenitrile (254909-28-9) → (2R,5S,6S)-6-(carbamoylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane (864381-62-4)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In ethanol; at 20 ℃; for 1h;

DOI:10.1039/b503994k

upstream raw materials:

(3R,7S,7aS)-7-Cyanomethyl-5-oxo-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazole-6-carboxylic acid ethyl ester

(2R,5S,6S,7S)-7-ethyloxycarbonyl-6-cyanomethyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

Downstream raw materials:

[(2S,3S)-3-(2-Amino-ethyl)-1-benzyl-pyrrolidin-2-yl]-methanol

(2R,5S,6S)-6-(carbamoylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

[2-((2S,3S)-2-Hydroxymethyl-5-oxo-pyrrolidin-3-yl)-ethyl]-carbamic acid benzyl ester

(2R,5S,6S)-6-(N-benzyloxycarbonyl-2-aminoethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

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