bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one

Base Information

Chemical Name:bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one
CAS No.:156045-79-3
Molecular Formula:C₁₂H₁₃NO₃
Molecular Weight:219.24
Hs Code.:

Synonyms:bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one

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Chemical Property of bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one

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Technology Process of bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one

There total 4 articles about bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-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: 95.0%

: 154631-82-0
(2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one

: 156045-79-3
bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one

Guidance literature:: With samarium diiodide; In tetrahydrofuran; methanol; at -78 ℃; for 0.5h;
DOI:10.1080/00397919708006067

Reference yield:

: 103201-79-2,1820583-17-2
(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 156045-79-3
bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) n-BuLi, hexamethyldisilazane / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h

2: 30percent aq. H₂O₂ / ethyl acetate / 0.67 h / 0 - 22 °C

3: 63 percent / t-BuOOH, n-Bu₄NF, K₂CO₃ / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h

4: 79 percent / aluminum amalgam, NaHCO₃ (half sat.) / ethanol; acetone / 2 h

With tert.-butylhydroperoxide; n-butyllithium; aluminium amalgam; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydrogencarbonate; potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; 2,2,4-trimethylpentane; ethanol; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0957-4166(00)80492-9

Reference yield:

: 134107-65-6
(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

: 156045-79-3
bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one

Guidance literature:: Multi-step reaction with 2 steps

1: 63 percent / t-BuOOH, n-Bu₄NF, K₂CO₃ / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h

2: 79 percent / aluminum amalgam, NaHCO₃ (half sat.) / ethanol; acetone / 2 h

With tert.-butylhydroperoxide; aluminium amalgam; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; 2,2,4-trimethylpentane; ethanol; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0957-4166(00)80492-9