(S)-3,3-bis(2,4,6-trimethylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-one

Base Information

• Chemical Name: (S)-3,3-bis(2,4,6-trimethylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-one
• CAS No.: 627503-43-9
• Molecular Formula: C₂₈H₃₇NO₂
• Molecular Weight: 419.607

Synonyms:(S)-3,3-bis(2,4,6-trimethylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-one

Chemical Property of (S)-3,3-bis(2,4,6-trimethylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-one

Chemical Property:

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Technology Process of (S)-3,3-bis(2,4,6-trimethylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-one

There total 2 articles about (S)-3,3-bis(2,4,6-trimethylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-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: 69.0%

2,4,6-trimethylbenzylbromide (4761-00-6) + (5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane (99208-71-6) → (S)-3,3-bis(2,4,6-trimethylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-one (627503-43-9)

Guidance literature:

(5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

2,4,6-trimethylbenzylbromide; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at 20 ℃; for 3h;

DOI:10.1021/jo035234q

Reference yield: 50.0%

(5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane (99208-71-6) → (S)-3,3-bis(2,4,6-trimethylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-one (627503-43-9)

Guidance literature:

(5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

2,4,6-trimethylbenzyl-X; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1002/adsc.200606058

Reference yield: 88.0%

(S)-3,3-bis(2,4,6-trimethylphenylmethyl)-8,8-dimethyl-7-oxa-1-azabicyclo[3.3.0]octan-2-one (627503-43-9) → (S)-3,3-bis(2,4,6-trimethylphenylmethyl)-5-hydroxymethylpyrrolidin-2-one (627503-49-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 3h; Heating;

DOI:10.1002/adsc.200606058

upstream raw materials:

2,4,6-trimethylbenzylbromide

(5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane

Downstream raw materials:

(S)-3,3-bis(2,4,6-trimethylphenylmethyl)-5-hydroxymethylpyrrolidin-2-one

(S)-(+)-(N-benzyloxycarbonyl)-(4,4-di(2,4,6-trimethylbenzyl)pyrrolidin-2-yl)methan-1-ol

(S)-1-[4,4-bis(2,4,6-trimethylphenylmethyl)-2-chloromethylpyrrolidin-1-yl]-2,2-dimethylpropan-1-one

(S)-1-[4,4-bis(2,4,6-trimethylphenylmethyl)-2-hydroxymethylpyrrolidin-1-yl]-2,2-dimethylpropan-1-one

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