(5-benzyloxy-7-oxo-2,3,7,8,9,9a-hexahydro-1-aza-phenalen-1-yl)-acetic acid methyl ester

Base Information

Chemical Name:(5-benzyloxy-7-oxo-2,3,7,8,9,9a-hexahydro-1-aza-phenalen-1-yl)-acetic acid methyl ester
CAS No.:306961-50-2
Molecular Formula:C₂₂H₂₃NO₄
Molecular Weight:365.429
Hs Code.:

Synonyms:(5-benzyloxy-7-oxo-2,3,7,8,9,9a-hexahydro-1-aza-phenalen-1-yl)-acetic acid methyl ester

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Chemical Property of (5-benzyloxy-7-oxo-2,3,7,8,9,9a-hexahydro-1-aza-phenalen-1-yl)-acetic acid methyl ester

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Technology Process of (5-benzyloxy-7-oxo-2,3,7,8,9,9a-hexahydro-1-aza-phenalen-1-yl)-acetic acid methyl ester

There total 14 articles about (5-benzyloxy-7-oxo-2,3,7,8,9,9a-hexahydro-1-aza-phenalen-1-yl)-acetic acid methyl ester 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: 54.0%

: 306961-48-8
3-[N-(methoxycarbonyl)methyl]-7-hydroxy-9-benzyloxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoline

: 306961-50-2
(5-benzyloxy-7-oxo-2,3,7,8,9,9a-hexahydro-1-aza-phenalen-1-yl)-acetic acid methyl ester

Guidance literature:: With Celite; sodium acetate; pyridinium chlorochromate; In dichloromethane; for 2h;
DOI:10.1021/jo991162k

Reference yield:

: 306961-29-5
1-(3-butenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

: 306961-50-2
(5-benzyloxy-7-oxo-2,3,7,8,9,9a-hexahydro-1-aza-phenalen-1-yl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 76 percent / triethylamine / CH₂Cl₂ / 2 h / -78 °C

2.1: m-CPBA / CH₂Cl₂ / 18 h / 20 °C

3.1: 73 percent / tin tetrachloride / CH₂Cl₂ / 3.5 h / -20 - 0 °C

4.1: 28.1 g / tri-tert-butylphosphine / tetrahydrofuran / 1 h / 20 °C

5.1: 12.0 g / m-CPBA; aq. NaHCO₃ / CH₂Cl₂ / 1.08 h / 0 - 20 °C

6.1: OsO₄ / dioxane; H₂O / 0.08 h / 20 °C

6.2: 53 percent / NaIO₄ / dioxane; H₂O / 3 h / 20 °C

7.1: 100 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C

8.1: BBr₃ / CH₂Cl₂ / 4.5 h / -78 - 20 °C

9.1: K₂CO₃ / dimethylsulfoxide / 20 h / 20 °C

10.1: 92 percent / LiAlH₄ / tetrahydrofuran; toluene / 4 h / Heating

11.1: KHCO₃ / tetrahydrofuran / 3 h / 0 - 20 °C

12.1: 54 percent / pyridinium chlorochromate; NaOAc; Celite / CH₂Cl₂ / 2 h

With osmium(VIII) oxide; lithium aluminium tetrahydride; tri-tert-butyl phosphine; Celite; sodium acetate; boron tribromide; tin(IV) chloride; sodium hydrogencarbonate; potassium carbonate; potassium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; 1.1: Addition / 2.1: Epoxidation / 3.1: Cyclization / 4.1: Substitution / 5.1: Oxidation / 6.1: Oxidation / 6.2: Oxidation / 7.1: Reduction / 8.1: demethylation / 9.1: Alkylation / 10.1: Reduction / 11.1: Alkylation / 12.1: Oxidation;
DOI:10.1021/jo991162k

Reference yield:

: 306961-28-4
1-but-3-enyl-6-methoxy-3,4-dihydro-isoquinoline

: 306961-50-2
(5-benzyloxy-7-oxo-2,3,7,8,9,9a-hexahydro-1-aza-phenalen-1-yl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 31.6 g / sodium cyanoborohydride / acetic acid / 2 h / 20 °C

2.1: 76 percent / triethylamine / CH₂Cl₂ / 2 h / -78 °C

3.1: m-CPBA / CH₂Cl₂ / 18 h / 20 °C

4.1: 73 percent / tin tetrachloride / CH₂Cl₂ / 3.5 h / -20 - 0 °C

5.1: 28.1 g / tri-tert-butylphosphine / tetrahydrofuran / 1 h / 20 °C

6.1: 12.0 g / m-CPBA; aq. NaHCO₃ / CH₂Cl₂ / 1.08 h / 0 - 20 °C

7.1: OsO₄ / dioxane; H₂O / 0.08 h / 20 °C

7.2: 53 percent / NaIO₄ / dioxane; H₂O / 3 h / 20 °C

8.1: 100 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C

9.1: BBr₃ / CH₂Cl₂ / 4.5 h / -78 - 20 °C

10.1: K₂CO₃ / dimethylsulfoxide / 20 h / 20 °C

11.1: 92 percent / LiAlH₄ / tetrahydrofuran; toluene / 4 h / Heating

12.1: KHCO₃ / tetrahydrofuran / 3 h / 0 - 20 °C

13.1: 54 percent / pyridinium chlorochromate; NaOAc; Celite / CH₂Cl₂ / 2 h

With osmium(VIII) oxide; lithium aluminium tetrahydride; tri-tert-butyl phosphine; Celite; sodium acetate; boron tribromide; tin(IV) chloride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; potassium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; toluene; 1.1: Reduction / 2.1: Addition / 3.1: Epoxidation / 4.1: Cyclization / 5.1: Substitution / 6.1: Oxidation / 7.1: Oxidation / 7.2: Oxidation / 8.1: Reduction / 9.1: demethylation / 10.1: Alkylation / 11.1: Reduction / 12.1: Alkylation / 13.1: Oxidation;
DOI:10.1021/jo991162k