(7S,8S,10bR)-7-(2-Bromo-6-methoxy-phenoxy)-8-hydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one

Base Information

Chemical Name:(7S,8S,10bR)-7-(2-Bromo-6-methoxy-phenoxy)-8-hydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one
CAS No.:207789-10-4
Molecular Formula:C₁₈H₂₀BrNO₅
Molecular Weight:410.264
Hs Code.:

Synonyms:

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Chemical Property of (7S,8S,10bR)-7-(2-Bromo-6-methoxy-phenoxy)-8-hydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one

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Technology Process of (7S,8S,10bR)-7-(2-Bromo-6-methoxy-phenoxy)-8-hydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one

There total 10 articles about (7S,8S,10bR)-7-(2-Bromo-6-methoxy-phenoxy)-8-hydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-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:

: 207789-04-6
(3aS,7aR)-6-Bromo-7-(2-bromo-ethyl)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxole

: 207789-10-4
(7S,8S,10bR)-7-(2-Bromo-6-methoxy-phenoxy)-8-hydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one

Guidance literature:: Multi-step reaction with 6 steps

1: 38 percent / NaH / dimethylsulfoxide / 1.) r.t., 15 min, 2.) r.t., overnight

2: 56 percent / Bu₃SnH, AIBN / benzene / 1 h / Heating

3: 94 percent / Dowex 50X₈-100 strongly acid resin / methanol; H₂O / Ambient temperature

4: 85.5 percent / i-PrNEt / CH₂Cl₂ / 4 h / -78 °C

5: 94 percent / DEAD, Bu₃P / tetrahydrofuran / 1.5 h / 0 °C

6: aq. TBAF, silica / tetrahydrofuran / 3.5 h / Ambient temperature

With 2,2'-azobis(isobutyronitrile); tributylphosphine; Dowex 50X₈-100 strongly acid resin; i-PrNEt; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; silica gel; sodium hydride; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; benzene;
DOI:10.1055/s-1998-5931

Reference yield:

: 172484-96-7
(1S,2R)-4-Bromo-3-(2-bromo-ethyl)-cyclohex-3-ene-1,2-diol

: 207789-10-4
(7S,8S,10bR)-7-(2-Bromo-6-methoxy-phenoxy)-8-hydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / p-TsOH / acetone / 3 h / Ambient temperature

2: 38 percent / NaH / dimethylsulfoxide / 1.) r.t., 15 min, 2.) r.t., overnight

3: 56 percent / Bu₃SnH, AIBN / benzene / 1 h / Heating

4: 94 percent / Dowex 50X₈-100 strongly acid resin / methanol; H₂O / Ambient temperature

5: 85.5 percent / i-PrNEt / CH₂Cl₂ / 4 h / -78 °C

6: 94 percent / DEAD, Bu₃P / tetrahydrofuran / 1.5 h / 0 °C

7: aq. TBAF, silica / tetrahydrofuran / 3.5 h / Ambient temperature

With 2,2'-azobis(isobutyronitrile); tributylphosphine; Dowex 50X₈-100 strongly acid resin; i-PrNEt; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; silica gel; sodium hydride; toluene-4-sulfonic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetone; benzene;
DOI:10.1055/s-1998-5931

Reference yield:

: 184884-49-9
(7S,8S,10bR)-7-(2-Bromo-6-methoxy-phenoxy)-8-(tert-butyl-dimethyl-silanyloxy)-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one

: 207789-10-4
(7S,8S,10bR)-7-(2-Bromo-6-methoxy-phenoxy)-8-hydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one

Guidance literature:: With tetrabutyl ammonium fluoride; silica gel; In tetrahydrofuran; for 3.5h; Yield given; Ambient temperature;
DOI:10.1055/s-1998-5931