(1S,5S,8S)-4-(4'-Bromophenyl)-8-hydroxy-2-oxa-3-azabicyclo[3.3.0]oct-3-en-6-one

Base Information

Chemical Name:(1S,5S,8S)-4-(4'-Bromophenyl)-8-hydroxy-2-oxa-3-azabicyclo[3.3.0]oct-3-en-6-one
CAS No.:325692-85-1
Molecular Formula:C₁₂H₁₀BrNO₃
Molecular Weight:296.12
Hs Code.:

Synonyms:(1S,5S,8S)-4-(4'-Bromophenyl)-8-hydroxy-2-oxa-3-azabicyclo[3.3.0]oct-3-en-6-one

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Chemical Property of (1S,5S,8S)-4-(4'-Bromophenyl)-8-hydroxy-2-oxa-3-azabicyclo[3.3.0]oct-3-en-6-one

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Technology Process of (1S,5S,8S)-4-(4'-Bromophenyl)-8-hydroxy-2-oxa-3-azabicyclo[3.3.0]oct-3-en-6-one

There total 5 articles about (1S,5S,8S)-4-(4'-Bromophenyl)-8-hydroxy-2-oxa-3-azabicyclo[3.3.0]oct-3-en-6-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: 52.0%

: 325692-79-3
(1S,5S,8S)-4-(4'-Bromophenyl)-8-(tert-butyldimethylsilyloxy)-2-oxa-3-azabicyclo[3.3.0]oct-3-en-6-one

: 325692-85-1
(1S,5S,8S)-4-(4'-Bromophenyl)-8-hydroxy-2-oxa-3-azabicyclo[3.3.0]oct-3-en-6-one

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 20 ℃; for 2.5h;
DOI:10.1039/b005520o

Reference yield:

: 56745-67-6,61305-35-9,61740-33-8,61305-36-0
(4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one

: 325692-85-1
(1S,5S,8S)-4-(4'-Bromophenyl)-8-hydroxy-2-oxa-3-azabicyclo[3.3.0]oct-3-en-6-one

Guidance literature:: Multi-step reaction with 2 steps

1: 73 percent / aq. NaOCl / CH₂Cl₂ / 18 h / 20 °C

2: 52 percent / aq. HF / acetonitrile / 2.5 h / 20 °C

With sodium hypochlorite; hydrogen fluoride; In dichloromethane; acetonitrile;
DOI:10.1039/b005520o

Reference yield:

: 60410-16-4
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

: 325692-85-1
(1S,5S,8S)-4-(4'-Bromophenyl)-8-hydroxy-2-oxa-3-azabicyclo[3.3.0]oct-3-en-6-one

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

2: 86 percent / K₂CO₃ / methanol / 1.5 h / 20 °C

3: 89 percent / PCC; CH₃COONa; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h / 20 °C

4: 73 percent / aq. NaOCl / CH₂Cl₂ / 18 h / 20 °C

5: 52 percent / aq. HF / acetonitrile / 2.5 h / 20 °C

With 1H-imidazole; sodium hypochlorite; 4 A molecular sieve; hydrogen fluoride; sodium acetate; potassium carbonate; pyridinium chlorochromate; In methanol; dichloromethane; acetonitrile;
DOI:10.1039/b005520o