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

Base Information

Chemical Name:methyl 9-O-tert-butyldimethylsilyl-10,11-dihydroquinidine-11-(phenoxy-p-carboxylate)
CAS No.:247096-94-2
Molecular Formula:C₃₄H₄₆N₂O₅Si
Molecular Weight:590.835
Hs Code.:

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

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

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

There total 6 articles about methyl 9-O-tert-butyldimethylsilyl-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: 98.0%

: 99-76-3,156291-94-0
methyl 4-hydroxylbenzoate

: 247096-93-1
9-O-tert-butyldimethylsilyl-10,11-dihydro-11-iodo-quinidine

: 247096-94-2
methyl 9-O-tert-butyldimethylsilyl-10,11-dihydroquinidine-11-(phenoxy-p-carboxylate)

Guidance literature:: With 18-crown-6 ether; potassium carbonate; In acetone; at 20 ℃;
DOI:10.1021/jo982496x

Reference yield:

: 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
quinindine

: 247096-94-2
methyl 9-O-tert-butyldimethylsilyl-10,11-dihydroquinidine-11-(phenoxy-p-carboxylate)

Guidance literature:: Multi-step reaction with 5 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

With dmap; borane-THF; 18-crown-6 ether; 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;
DOI:10.1021/jo982496x

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 247096-94-2
methyl 9-O-tert-butyldimethylsilyl-10,11-dihydroquinidine-11-(phenoxy-p-carboxylate)

Guidance literature:: Multi-step reaction with 5 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

With dmap; borane-THF; 18-crown-6 ether; 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;
DOI:10.1021/jo982496x