2,8-diketo-11-isopropylidene-10-(4-methoxyphenyl)3,9-diazatricyclo<5.3.2.0^3,7>dodecane

Base Information

• Chemical Name: 2,8-diketo-11-isopropylidene-10-(4-methoxyphenyl)3,9-diazatricyclo<5.3.2.0^3,7>dodecane
• CAS No.: 124316-32-1
• Molecular Formula: C₂₀H₂₄N₂O₃
• Molecular Weight: 340.422

Synonyms:2,8-diketo-11-isopropylidene-10-(4-methoxyphenyl)3,9-diazatricyclo<5.3.2.0^3,7>dodecane

Chemical Property of 2,8-diketo-11-isopropylidene-10-(4-methoxyphenyl)3,9-diazatricyclo<5.3.2.0^3,7>dodecane

Chemical Property:

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Technology Process of 2,8-diketo-11-isopropylidene-10-(4-methoxyphenyl)3,9-diazatricyclo<5.3.2.0^3,7>dodecane

There total 9 articles about 2,8-diketo-11-isopropylidene-10-(4-methoxyphenyl)3,9-diazatricyclo<5.3.2.0^3,7>dodecane 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: 22.0%

2,8-diketo-10-isopropylidene-9-(4-methoxybenzyl)-3,9-diazatricyclo<5.2.2.03,7>undecane (124268-75-3) → 2,8-diketo-11-isopropylidene-10-(4-methoxyphenyl)3,9-diazatricyclo<5.3.2.03,7>dodecane (124316-32-1)

Guidance literature:

With n-butyllithium; N,N-dimethyl-formamide; 1.) THF, hexane, -78 deg C, 20 min, 2.) -78 deg C, 30 min;

Reference yield:

(2R,5R)-5-allyl-2-tert-butyl-1-aza-3-oxabicyclo<3.3.0>octan-4-one (81286-83-1) → 2,8-diketo-11-isopropylidene-10-(4-methoxyphenyl)3,9-diazatricyclo<5.3.2.03,7>dodecane (124316-32-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1.5 h

2: 1.) K₂CO₃, 2.) 50percent aq. NaOH / 1.) methylene chloride, 0 deg C, 1 h, 2.) 8 h

3: 1.) ozone, 2.) dimethyl sulfide / 1.) MeOH, -78 deg C, 1 h

4: 1,2-dichloro-benzene / 3 h / 115 °C

5: 96.5 percent / NaBH₄ / ethanol / 0.33 h / 35 - 50 °C

6: collidine, LiCl, methanesulfonyl chloride / dimethylformamide / 4 h / 25 °C

7: 37 percent / NaH / dimethylformamide / 11 h / 25 °C

8: 22 percent / 1.) n-BuLi, 2.) DMF / 1.) THF, hexane, -78 deg C, 20 min, 2.) -78 deg C, 30 min

With 2,3,5-trimethyl-pyridine; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; sodium hydride; potassium carbonate; ozone; methanesulfonyl chloride; N,N-dimethyl-formamide; lithium chloride; In ethanol; N,N-dimethyl-formamide; 1,2-dichloro-benzene;

Reference yield:

(-)-2-(R)-allyl-2-<(4-methoxybenzyl)carboxamido>pyrrolidine (116005-51-7) → 2,8-diketo-11-isopropylidene-10-(4-methoxyphenyl)3,9-diazatricyclo<5.3.2.03,7>dodecane (124316-32-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) K₂CO₃, 2.) 50percent aq. NaOH / 1.) methylene chloride, 0 deg C, 1 h, 2.) 8 h

2: 1.) ozone, 2.) dimethyl sulfide / 1.) MeOH, -78 deg C, 1 h

3: 1,2-dichloro-benzene / 3 h / 115 °C

4: 96.5 percent / NaBH₄ / ethanol / 0.33 h / 35 - 50 °C

5: collidine, LiCl, methanesulfonyl chloride / dimethylformamide / 4 h / 25 °C

6: 37 percent / NaH / dimethylformamide / 11 h / 25 °C

7: 22 percent / 1.) n-BuLi, 2.) DMF / 1.) THF, hexane, -78 deg C, 20 min, 2.) -78 deg C, 30 min

With 2,3,5-trimethyl-pyridine; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; sodium hydride; potassium carbonate; ozone; methanesulfonyl chloride; N,N-dimethyl-formamide; lithium chloride; In ethanol; N,N-dimethyl-formamide; 1,2-dichloro-benzene;

upstream raw materials:

2,8-diketo-10-isopropylidene-9-(4-methoxybenzyl)-3,9-diazatricyclo<5.2.2.0^3,7>undecane

(2R,5R)-5-allyl-2-tert-butyl-1-aza-3-oxabicyclo<3.3.0>octan-4-one

(-)-2-(R)-allyl-2-<(4-methoxybenzyl)carboxamido>pyrrolidine

(-)-2,5-diketo-6-(R)-allyl-4-(methoxybenzyl)-1,4-diazabicyclo<4.3.0>nonane

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