(+/-)-O-benzylmontanine

Base Information

Chemical Name:(+/-)-O-benzylmontanine
CAS No.:139025-49-3
Molecular Formula:C₂₄H₂₅NO₄
Molecular Weight:391.467
Hs Code.:

Synonyms:

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Chemical Property of (+/-)-O-benzylmontanine

Chemical Property:

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Technology Process of (+/-)-O-benzylmontanine

There total 62 articles about (+/-)-O-benzylmontanine 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: 79.0%

: 144609-85-8
(3R*,4aR*,11R*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-2,2-dimethoxy-Δ^1(11a)-8,9-(methylenedioxy)-5,11-methanomorphanthridine

: 139025-49-3,144609-93-8
(+/-)-O-benzylcoccinine

Guidance literature:: With diisobutylaluminium hydride; In toluene; for 1h; Ambient temperature;
DOI:10.1021/jo00052a051

Reference yield:

: 17680-04-5
(3,4-methylenedioxy)phenylmagnesium bromide

: 139025-49-3,144609-93-8
(+/-)-O-benzylcoccinine

Guidance literature:: Multi-step reaction with 21 steps

1: 95.6 percent / tetrahydrofuran / 0.17 h / ice-cooling

2: 1) Et₃N, ethyl chloroformate, 2) NaN₃ / 1) acetone, ice-cooling, 0.5 h, 2) acetone, water, ice-cooling, 1 h

3: 16 h / Heating

4: trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

5: Et₃N / CHCl₃ / 1 h / Ambient temperature

6: 100 percent / N-methylmorpholine N-oxide / OsO₄ / dioxane / 2 h / Ambient temperature

7: 92.7 percent / pyridine / DMAP / 2 h / Ambient temperature

8: 1) t-BuOK / 1) THF, room temperature, 0.5 h, 2) room temperature, 2 h

9: 1) BH₃*THF, 2) 3 M aq. NaOH, 30percent aq. H₂O₂ / 1) THF, ice-cooling, 4 h, 2) water, room temperature, 40 min

10: 100 percent / pyridine / 1 h / Ambient temperature

11: 80.6 percent / methanesulfonic acid, Ac₂O / 1,2-dichloro-ethane / 2 h / Ambient temperature

12: 100 percent / NaOMe / methanol / 0.33 h / Ambient temperature

13: 82.5 percent / p-TsOH*H₂O / CHCl₃ / 1.33 h / Ambient temperature

14: 90.7 percent / sodium bis(2-methoxyethoxy)aluminum hydride / o-xylene / 0.58 h / Heating

15: 74.6 percent / diisobutylaluminum hydride / toluene / 2 h / Ambient temperature

16: 100 percent / Et₃N / CH₂Cl₂ / 0.17 h / ice-cooling

17: 33 percent / DBU / o-xylene / 2.5 h / Ambient temperature

18: 1) PhSeCl, 2) NaIO₄ / 1) MeOH, 15-20 deg C, sonication, 2 h, 2) H₂O, 10 min

19: 31.2 percent / bis(tetrabutylammonium) dichromate / CHCl₃ / 3 h / Heating

20: 99.1 percent / p-TsOH*H₂O / methanol / 2 h / Ambient temperature

21: 79 percent / diisobutylaluminum hydride / toluene / 1 h / Ambient temperature

With pyridine; sodium hydroxide; sodium periodate; sodium azide; Phenylselenyl chloride; borane-THF; tetra(n-butyl)ammonium dichromate(VI); methanesulfonic acid; potassium tert-butylate; dihydrogen peroxide; sodium methylate; chloroformic acid ethyl ester; acetic anhydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; dmap; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; o-xylene; 1,2-dichloro-ethane; toluene;
DOI:10.1021/jo00052a051

Reference yield:

: 139025-41-5
(1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid

: 139025-49-3,144609-93-8
(+/-)-O-benzylcoccinine

Guidance literature:: Multi-step reaction with 20 steps

1: 1) Et₃N, ethyl chloroformate, 2) NaN₃ / 1) acetone, ice-cooling, 0.5 h, 2) acetone, water, ice-cooling, 1 h

2: 16 h / Heating

3: trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

4: Et₃N / CHCl₃ / 1 h / Ambient temperature

5: 100 percent / N-methylmorpholine N-oxide / OsO₄ / dioxane / 2 h / Ambient temperature

6: 92.7 percent / pyridine / DMAP / 2 h / Ambient temperature

7: 1) t-BuOK / 1) THF, room temperature, 0.5 h, 2) room temperature, 2 h

8: 1) BH₃*THF, 2) 3 M aq. NaOH, 30percent aq. H₂O₂ / 1) THF, ice-cooling, 4 h, 2) water, room temperature, 40 min

9: 100 percent / pyridine / 1 h / Ambient temperature

10: 80.6 percent / methanesulfonic acid, Ac₂O / 1,2-dichloro-ethane / 2 h / Ambient temperature

11: 100 percent / NaOMe / methanol / 0.33 h / Ambient temperature

12: 82.5 percent / p-TsOH*H₂O / CHCl₃ / 1.33 h / Ambient temperature

13: 90.7 percent / sodium bis(2-methoxyethoxy)aluminum hydride / o-xylene / 0.58 h / Heating

14: 74.6 percent / diisobutylaluminum hydride / toluene / 2 h / Ambient temperature

15: 100 percent / Et₃N / CH₂Cl₂ / 0.17 h / ice-cooling

16: 33 percent / DBU / o-xylene / 2.5 h / Ambient temperature

17: 1) PhSeCl, 2) NaIO₄ / 1) MeOH, 15-20 deg C, sonication, 2 h, 2) H₂O, 10 min

18: 31.2 percent / bis(tetrabutylammonium) dichromate / CHCl₃ / 3 h / Heating

19: 99.1 percent / p-TsOH*H₂O / methanol / 2 h / Ambient temperature

20: 79 percent / diisobutylaluminum hydride / toluene / 1 h / Ambient temperature

With pyridine; sodium hydroxide; sodium periodate; sodium azide; Phenylselenyl chloride; borane-THF; tetra(n-butyl)ammonium dichromate(VI); methanesulfonic acid; potassium tert-butylate; dihydrogen peroxide; sodium methylate; chloroformic acid ethyl ester; acetic anhydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; dmap; osmium(VIII) oxide; In 1,4-dioxane; methanol; dichloromethane; chloroform; o-xylene; 1,2-dichloro-ethane; toluene;
DOI:10.1021/jo00052a051