(5-{2-[((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amino]-ethyl}-1,3-dihydro-isoindol-2-yl)-phenyl-methanone

Base Information

Chemical Name:(5-{2-[((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amino]-ethyl}-1,3-dihydro-isoindol-2-yl)-phenyl-methanone
CAS No.:152149-19-4
Molecular Formula:C₃₀H₃₄N₂O₂
Molecular Weight:454.612
Hs Code.:

Synonyms:(5-{2-[((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amino]-ethyl}-1,3-dihydro-isoindol-2-yl)-phenyl-methanone

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Chemical Property of (5-{2-[((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amino]-ethyl}-1,3-dihydro-isoindol-2-yl)-phenyl-methanone

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Technology Process of (5-{2-[((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amino]-ethyl}-1,3-dihydro-isoindol-2-yl)-phenyl-methanone

There total 20 articles about (5-{2-[((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amino]-ethyl}-1,3-dihydro-isoindol-2-yl)-phenyl-methanone 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:

: 66826-78-6
5-bromo-2,3-dihydrobenzo[b]furan

: 152149-19-4
(5-{2-[((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amino]-ethyl}-1,3-dihydro-isoindol-2-yl)-phenyl-methanone

Guidance literature:: Multi-step reaction with 19 steps

1: 19.5 g / AlCl₃ / CH₂Cl₂ / 16 h / Ambient temperature

2: 12.4 g / H₂ / 10percent Pd/C / ethanol / 3040 Torr

3: 10.9 g / aq. KOH / ethanol / 3 h / Ambient temperature

4: 7.6 g / PPA / 0.33 h / 100 °C

5: LiCN / tetrahydrofuran / 0.75 h / 5 °C

6: p-TsOH / benzene / 2 h / Heating

7: NaBH₄ / ethanol / 1 h / Heating

8: 45percent aq. KOH / ethane-1,2-diol / 20 h / Heating

9: oxalyl chloride, DMF / toluene / 1.5 h / 50 °C

10: 1.) EtMe₂N / 1.) toluene, RT, 3 h, 2.) toluene, from -70 to -30 deg C, 2 h

11: LiAlH₄ / tetrahydrofuran / 1 h

12: NEt₃ / CH₂Cl₂ / 1 h / 0 °C

13: 48 h / 25 °C

14: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole / tetrahydrofuran / 18 h / Ambient temperature

15: 0.31 g / DDQ / dioxane / 4 h / Heating

16: BH₃*THF / tetrahydrofuran / 3 h / Heating

17: 2.00 g / aq. LiOH / tetrahydrofuran

18: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole / tetrahydrofuran / 18 h / Ambient temperature

19: BH₃*THF / tetrahydrofuran / 5 h / Heating

With potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; aluminium trichloride; borane-THF; oxalyl dichloride; N,N-dimethyl-ethanamine; lithium cyanide; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; ethylene glycol; toluene; benzene;
DOI:10.1021/jm960723m

Reference yield:

: 188111-32-2
4-(5-Bromo-2,3-dihydro-benzofuran-6-yl)-4-oxo-butyric acid ethyl ester

: 152149-19-4
(5-{2-[((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amino]-ethyl}-1,3-dihydro-isoindol-2-yl)-phenyl-methanone

Guidance literature:: Multi-step reaction with 18 steps

1: 12.4 g / H₂ / 10percent Pd/C / ethanol / 3040 Torr

2: 10.9 g / aq. KOH / ethanol / 3 h / Ambient temperature

3: 7.6 g / PPA / 0.33 h / 100 °C

4: LiCN / tetrahydrofuran / 0.75 h / 5 °C

5: p-TsOH / benzene / 2 h / Heating

6: NaBH₄ / ethanol / 1 h / Heating

7: 45percent aq. KOH / ethane-1,2-diol / 20 h / Heating

8: oxalyl chloride, DMF / toluene / 1.5 h / 50 °C

9: 1.) EtMe₂N / 1.) toluene, RT, 3 h, 2.) toluene, from -70 to -30 deg C, 2 h

10: LiAlH₄ / tetrahydrofuran / 1 h

11: NEt₃ / CH₂Cl₂ / 1 h / 0 °C

12: 48 h / 25 °C

13: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole / tetrahydrofuran / 18 h / Ambient temperature

14: 0.31 g / DDQ / dioxane / 4 h / Heating

15: BH₃*THF / tetrahydrofuran / 3 h / Heating

16: 2.00 g / aq. LiOH / tetrahydrofuran

17: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole / tetrahydrofuran / 18 h / Ambient temperature

18: BH₃*THF / tetrahydrofuran / 5 h / Heating

With potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; N,N-dimethyl-ethanamine; lithium cyanide; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; ethylene glycol; toluene; benzene;
DOI:10.1021/jm960723m