(1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(methoxymethylene)-7-azabicyclo[4.2.1]nonane-8-one

Base Information

Chemical Name:(1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(methoxymethylene)-7-azabicyclo[4.2.1]nonane-8-one
CAS No.:199103-51-0
Molecular Formula:C₁₉H₂₅NO₄
Molecular Weight:331.412
Hs Code.:

Synonyms:(1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(methoxymethylene)-7-azabicyclo[4.2.1]nonane-8-one

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Chemical Property of (1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(methoxymethylene)-7-azabicyclo[4.2.1]nonane-8-one

Chemical Property:

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Technology Process of (1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(methoxymethylene)-7-azabicyclo[4.2.1]nonane-8-one

There total 10 articles about (1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(methoxymethylene)-7-azabicyclo[4.2.1]nonane-8-one 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: 91.0%

: 199103-49-6
(1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(hydroxymethylene)-7-azabicyclo[4.2.1]nonane-8-one

: 74-88-4
methyl iodide

: 199103-51-0
(1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(methoxymethylene)-7-azabicyclo[4.2.1]nonane-8-one

Guidance literature:: With sodium hydride; In tetrahydrofuran; for 18h; Ambient temperature;
DOI:10.1021/jo971510n

Reference yield:

: 129823-21-8,173353-34-9
(S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione

: 199103-51-0
(1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(methoxymethylene)-7-azabicyclo[4.2.1]nonane-8-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) -35 deg C, 1 h, 2.) -50 deg C to -25 deg C, 30 min, rt, 18 h

2: 1.) LDA / 1.) THF, hexane, -20 deg C, 1 h, 2.) THF, hexane, -117 deg C, 6 h, rt, 18 h

3: 2.) NH₃ / 1.) HCO₂H, 85 deg C, 2.5 d, 2.) MeOH, rt, 1 h

4: 99 percent / p-TsOH / benzene

5: 1.) (ClCO)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h, 2. ) CH₂Cl₂, rt, 15 min

6: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 25 min, 2.) THF, hexane, reflux, 18 h

7: 1.) BH₃*SMe₂, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C -> rt, 2 h, 2.) H₂O, rt, 1 h

8: 91 percent / NaH / tetrahydrofuran / 18 h / Ambient temperature

With sodium hydroxide; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; ammonia; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; benzene;
DOI:10.1021/jo971510n

Reference yield:

: 188295-12-7
(S)-1-Benzyl-5-ethoxy-4-hydroxy-pyrrolidin-2-one

: 199103-51-0
(1S,6R,9R)-7-benzyl-4,4-(ethylenedioxy)-9-(methoxymethylene)-7-azabicyclo[4.2.1]nonane-8-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) LDA / 1.) THF, hexane, -20 deg C, 1 h, 2.) THF, hexane, -117 deg C, 6 h, rt, 18 h

2: 2.) NH₃ / 1.) HCO₂H, 85 deg C, 2.5 d, 2.) MeOH, rt, 1 h

3: 99 percent / p-TsOH / benzene

4: 1.) (ClCO)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h, 2. ) CH₂Cl₂, rt, 15 min

5: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 25 min, 2.) THF, hexane, reflux, 18 h

6: 1.) BH₃*SMe₂, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C -> rt, 2 h, 2.) H₂O, rt, 1 h

7: 91 percent / NaH / tetrahydrofuran / 18 h / Ambient temperature

With sodium hydroxide; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; ammonia; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; benzene;
DOI:10.1021/jo971510n