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

Base Information

• Chemical Name: 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyloxy-quinidine
• CAS No.: 247096-92-0
• Molecular Formula: C₃₃H₄₆N₂O₅SSi
• Molecular Weight: 610.89
• Mol file: 247096-92-0.mol

Synonyms:9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyloxy-quinidine

Chemical Property of 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyloxy-quinidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyloxy-quinidine

There total 4 articles about 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyloxy-quinidine 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: 77.0%

p-toluenesulfonyl chloride (98-59-9) + 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-hydroxyquinidine (247096-89-5) → 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyloxy-quinidine (247096-92-0)

Guidance literature:

With triethylamine; In dichloromethane; 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) → 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyloxy-quinidine (247096-92-0)

Guidance literature:

Multi-step reaction with 3 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

With dmap; borane-THF; triethylamine; In tetrahydrofuran; dichloromethane; diethylene glycol dimethyl ether; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Addition / 2.2: Oxidation / 3.1: Tosylation;

DOI:10.1021/jo982496x

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyloxy-quinidine (247096-92-0)

Guidance literature:

Multi-step reaction with 3 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

With dmap; borane-THF; triethylamine; In tetrahydrofuran; dichloromethane; diethylene glycol dimethyl ether; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Addition / 2.2: Oxidation / 3.1: Tosylation;

DOI:10.1021/jo982496x

upstream raw materials:

p-toluenesulfonyl chloride

9-O-tert-butyldimethylsilyl-10,11-dihydro-11-hydroxyquinidine

quinindine

tert-butyldimethylsilyl chloride

Downstream raw materials:

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

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