6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

Base Information

Chemical Name:6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile
CAS No.:186355-26-0
Molecular Formula:C₂₃H₃₁N₃O₂Si
Molecular Weight:409.604
Hs Code.:

6-amino-7-benzyloxy-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

Synonyms:6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

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Chemical Property of 6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

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Technology Process of 6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

There total 19 articles about 6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile 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: 65.0%

: 174873-46-2
1-benzoyl-6-(benzoylamino)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-5-cyano-1,2,3,4-tetrahydroquinoline

: 6-amino-7-benzyloxy-3-hydroxy-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

: 186355-26-0
6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

Guidance literature:: With hydrazine; In ethanol; at 140 ℃; for 20h;
DOI:10.1021/ja962431g

Reference yield:

: 100-44-7
benzyl chloride

: 186355-26-0
6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

Guidance literature:: Multi-step reaction with 13 steps

1.1: 94 percent

2.1: 100 percent / NBS

3.1: 95 percent

4.1: 100 percent / Al-Hg

5.1: 96 percent

6.1: 84 percent / Pb(OAc)4 / 4 h / 25 °C

7.1: BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -20 °C

7.2: 89 percent / CH₂Cl₂ / 3 h / -20 °C

8.1: 95 percent / N-methylmorpholine N-oxide / OsO₄ / acetone; H₂O; toluene / 25 °C

9.1: Bu₂SnO / toluene; tetrahydrofuran / 6 h / Heating

9.2: 94 percent / Et₃N / toluene / 12 h / 25 °C

10.1: 75 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

11.1: 97 percent / NaH / tetrahydrofuran / 2 h / 0 °C

12.1: 45 percent / NH₂NH₂ / ethanol / 20 h / 140 °C

13.1: 2,6-lutidine / CH₂Cl₂

13.2: water; citric acid

With 2,6-dimethylpyridine; lead(IV) acetate; N-Bromosuccinimide; aluminium amalgam; boron trifluoride diethyl etherate; sodium hydride; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; hydrazine; osmium(VIII) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene; 1.1: Alkylation / 2.1: Bromination / 3.1: Substitution / 4.1: Reduction / 5.1: Acylation / 6.1: Oxidation / 7.1: Addition / 7.2: Addition / 8.1: hydroxylation / 9.1: Addition / 9.2: Tosylation / 10.1: silylation / 11.1: Cyclization / 12.1: deprotection / 13.1: silylation / 13.2: Hydrolysis;
DOI:10.1021/ja962431g

Reference yield:

: 127028-17-5
2-(benzyloxy)-6-bromo-4-nitro-aniline

: 186355-26-0
6-amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile

Guidance literature:: Multi-step reaction with 11 steps

1.1: 95 percent

2.1: 100 percent / Al-Hg

3.1: 96 percent

4.1: 84 percent / Pb(OAc)4 / 4 h / 25 °C

5.1: BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -20 °C

5.2: 89 percent / CH₂Cl₂ / 3 h / -20 °C

6.1: 95 percent / N-methylmorpholine N-oxide / OsO₄ / acetone; H₂O; toluene / 25 °C

7.1: Bu₂SnO / toluene; tetrahydrofuran / 6 h / Heating

7.2: 94 percent / Et₃N / toluene / 12 h / 25 °C

8.1: 75 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

9.1: 97 percent / NaH / tetrahydrofuran / 2 h / 0 °C

10.1: 45 percent / NH₂NH₂ / ethanol / 20 h / 140 °C

11.1: 2,6-lutidine / CH₂Cl₂

11.2: water; citric acid

With 2,6-dimethylpyridine; lead(IV) acetate; aluminium amalgam; boron trifluoride diethyl etherate; sodium hydride; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; hydrazine; osmium(VIII) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene; 1.1: Substitution / 2.1: Reduction / 3.1: Acylation / 4.1: Oxidation / 5.1: Addition / 5.2: Addition / 6.1: hydroxylation / 7.1: Addition / 7.2: Tosylation / 8.1: silylation / 9.1: Cyclization / 10.1: deprotection / 11.1: silylation / 11.2: Hydrolysis;
DOI:10.1021/ja962431g