(-)-(3S,4R)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline

Base Information

• Chemical Name: (-)-(3S,4R)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline
• CAS No.: 155158-71-7
• Molecular Formula: C₂₅H₂₃BrF₃NO₅
• Molecular Weight: 554.361
• Mol file: 155158-71-7.mol

Synonyms:

Chemical Property of (-)-(3S,4R)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3S,4R)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline

There total 5 articles about (-)-(3S,4R)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline 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: 40.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + (+/-)-trans-3-bromo-4-hydroxy-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline → (+)-(3R,4S)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline (155102-07-1) + (-)-(3S,4R)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline (155158-71-7)

Guidance literature:

DOI:10.1039/b005285j

Reference yield:

5-methoxy-2,2-dimethyl-(2H)-pyrano<2,3-b>quinoline (88148-18-9) → (-)-(3S,4R)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline (155158-71-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / N-bromosuccinimide; water / tetrahydrofuran / 24 h / 20 °C

2: 36 percent

With N-Bromosuccinimide; water; In tetrahydrofuran; 1: Addition / 2: Acylation;

DOI:10.1039/b005285j

Reference yield:

atanine (7282-19-1) → (-)-(3S,4R)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline (155158-71-7)

Guidance literature:

Multi-step reaction with 4 steps

1: NBS / diethyl ether

2: NaOMe / methanol

3: 78 percent / N-bromosuccinimide; water / tetrahydrofuran / 24 h / 20 °C

4: 36 percent

With N-Bromosuccinimide; water; sodium methylate; In tetrahydrofuran; methanol; diethyl ether; 1: Cyclization / 2: Dehydrobromination / 3: Addition / 4: Acylation;

DOI:10.1039/b005285j

upstream raw materials:

(R)-methoxytrifluoromethylphenylacetyl chloride

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

atanine

5-methoxy-2,2-dimethyl-(2H)-pyrano<2,3-b>quinoline

Downstream raw materials:

(+)-(3R)-ribalinine