methyl 10,11-dihydroquinidine-11-(phenoxy-p-carboxylate)

Base Information

• Chemical Name: methyl 10,11-dihydroquinidine-11-(phenoxy-p-carboxylate)
• CAS No.: 219596-40-4
• Molecular Formula: C₂₈H₃₂N₂O₅
• Molecular Weight: 476.572
• Mol file: 219596-40-4.mol

Synonyms:methyl 10,11-dihydroquinidine-11-(phenoxy-p-carboxylate)

Chemical Property of methyl 10,11-dihydroquinidine-11-(phenoxy-p-carboxylate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 10,11-dihydroquinidine-11-(phenoxy-p-carboxylate)

There total 6 articles about methyl 10,11-dihydroquinidine-11-(phenoxy-p-carboxylate) 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: 45.0%

methyl 9-O-tert-butyldimethylsilyl-10,11-dihydroquinidine-11-(phenoxy-p-carboxylate) (247096-94-2) → methyl 10,11-dihydroquinidine-11-(phenoxy-p-carboxylate) (219596-40-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo982496x

Reference yield:

quinindine (56-54-2,130-95-0,572-59-8,572-60-1,42151-59-7,47342-58-5,72402-50-7,72402-51-8,72402-52-9,72402-53-0,101143-86-6,101143-87-7,101143-88-8,146925-10-2) → methyl 10,11-dihydroquinidine-11-(phenoxy-p-carboxylate) (219596-40-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / Et₃N; DMAP / dimethylformamide

2.1: BH₃*THF / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 0.5 h / 0 °C

2.2: 81 percent / triethylamine N-oxide dihydrate / 1 h / 100 °C

3.1: 77 percent / Et₃N / CH₂Cl₂ / 20 °C

4.1: 79 percent / NaI / acetone / 60 °C / Heating

5.1: 98 percent / 18-crown-6; K₂CO₃ / acetone / 20 °C

6.1: 45 percent / TBAF / tetrahydrofuran / 20 °C

With dmap; borane-THF; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; diethylene glycol dimethyl ether; N,N-dimethyl-formamide; acetone; 1.1: Substitution / 2.1: Addition / 2.2: Oxidation / 3.1: Tosylation / 4.1: Iodination / 5.1: Substitution / 6.1: Substitution;

DOI:10.1021/jo982496x

Reference yield:

(3R,4S,8R,9S)-9-{[tert-butyl(dimethyl)silyl]oxy}-6'-methoxycinchonan (205432-44-6) → methyl 10,11-dihydroquinidine-11-(phenoxy-p-carboxylate) (219596-40-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BH₃*THF / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 0.5 h / 0 °C

1.2: 81 percent / triethylamine N-oxide dihydrate / 1 h / 100 °C

2.1: 77 percent / Et₃N / CH₂Cl₂ / 20 °C

3.1: 79 percent / NaI / acetone / 60 °C / Heating

4.1: 98 percent / 18-crown-6; K₂CO₃ / acetone / 20 °C

5.1: 45 percent / TBAF / tetrahydrofuran / 20 °C

With borane-THF; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; diethylene glycol dimethyl ether; acetone; 1.1: Addition / 1.2: Oxidation / 2.1: Tosylation / 3.1: Iodination / 4.1: Substitution / 5.1: Substitution;

DOI:10.1021/jo982496x

upstream raw materials:

methyl 9-O-tert-butyldimethylsilyl-10,11-dihydroquinidine-11-(phenoxy-p-carboxylate)

quinindine

(3R,4S,8R,9S)-9-{[tert-butyl(dimethyl)silyl]oxy}-6'-methoxycinchonan

9-O-tert-butyldimethylsilyl-10,11-dihydro-11-iodo-quinidine