9-(benzyloxy)-8-cyano-1-ethoxy-3-(hydroxymethyl)-7,8-dihydro-6H-cyclopentisoquinoline

Base Information

Chemical Name:9-(benzyloxy)-8-cyano-1-ethoxy-3-(hydroxymethyl)-7,8-dihydro-6H-cyclopentisoquinoline
CAS No.:172268-85-8
Molecular Formula:C₂₃H₂₂N₂O₃
Molecular Weight:374.439
Hs Code.:

9-(benzyloxy)-8-cyano-1-ethoxy-3-(hydroxymethyl)-7,8-dihydro-6H-cyclopent<g>isoquinoline

Synonyms:9-(benzyloxy)-8-cyano-1-ethoxy-3-(hydroxymethyl)-7,8-dihydro-6H-cyclopentisoquinoline

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Chemical Property of 9-(benzyloxy)-8-cyano-1-ethoxy-3-(hydroxymethyl)-7,8-dihydro-6H-cyclopentisoquinoline

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Technology Process of 9-(benzyloxy)-8-cyano-1-ethoxy-3-(hydroxymethyl)-7,8-dihydro-6H-cyclopentisoquinoline

There total 8 articles about 9-(benzyloxy)-8-cyano-1-ethoxy-3-(hydroxymethyl)-7,8-dihydro-6H-cyclopentisoquinoline 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: 92.0%

: 172268-84-7
9-(benzyloxy)-8-cyano-1-ethoxy-3-(ethoxycarbonyl)-7,8-dihydro-6H-cyclopentisoquinoline

: 172268-86-9
9-(benzyloxy)-8-cyano-1-ethoxy-7,8-dihydro-6H-cyclopentisoquinoline-3-carboxaldehyde

: 172268-85-8
9-(benzyloxy)-8-cyano-1-ethoxy-3-(hydroxymethyl)-7,8-dihydro-6H-cyclopentisoquinoline

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 3h;
DOI:10.1021/ja00153a004

Reference yield:

: 141903-26-6
3,6-bis(ethoxycarbonyl)-2-ethoxy-4-methylpyridine

: 172268-85-8
9-(benzyloxy)-8-cyano-1-ethoxy-3-(hydroxymethyl)-7,8-dihydro-6H-cyclopentisoquinoline

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) LDA, 3.) EtOH

2: 87 percent / DDQ / CH₂Cl₂ / 0.17 h / 25 °C

3: 93 percent / K₂CO₃, Bu₄NI / dimethylformamide / 6 h / 25 °C

4: t-BuOK, EtOH / CH₂Cl₂ / 7 h / -67 - 25 °C

5: 68 percent / Et₃N, DMAP

6: 92 percent / Dibal-H / tetrahydrofuran; toluene / 3 h / -78 °C

With dmap; ethanol; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00153a004

Reference yield:

: 1035804-85-3
3,6-bis(ethoxycarbonyl)-2,2-diethoxy-4-methyl-1-(methylsulfonyl)-1,2,3,4-tetrahydropyridine

: 172268-85-8
9-(benzyloxy)-8-cyano-1-ethoxy-3-(hydroxymethyl)-7,8-dihydro-6H-cyclopentisoquinoline

Guidance literature:: Multi-step reaction with 7 steps

1: 83 percent / DBU / tetrahydrofuran / 40 h / 70 °C

2: 1.) LDA, 3.) EtOH

3: 87 percent / DDQ / CH₂Cl₂ / 0.17 h / 25 °C

4: 93 percent / K₂CO₃, Bu₄NI / dimethylformamide / 6 h / 25 °C

5: t-BuOK, EtOH / CH₂Cl₂ / 7 h / -67 - 25 °C

6: 68 percent / Et₃N, DMAP

7: 92 percent / Dibal-H / tetrahydrofuran; toluene / 3 h / -78 °C

With dmap; ethanol; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00153a004