methyl 2-aza-3-methyl-4-(methoxymethoxy)-9-oxo-7-[(phenylsulfonyl)phenylthiomethyl]bicyclo[4.4.0]decane-2-carboxylate

Base Information

Chemical Name:methyl 2-aza-3-methyl-4-(methoxymethoxy)-9-oxo-7-[(phenylsulfonyl)phenylthiomethyl]bicyclo[4.4.0]decane-2-carboxylate
CAS No.:224184-04-7
Molecular Formula:C₂₇H₃₃NO₇S₂
Molecular Weight:547.694
Hs Code.:

Synonyms:methyl 2-aza-3-methyl-4-(methoxymethoxy)-9-oxo-7-[(phenylsulfonyl)phenylthiomethyl]bicyclo[4.4.0]decane-2-carboxylate

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Chemical Property of methyl 2-aza-3-methyl-4-(methoxymethoxy)-9-oxo-7-[(phenylsulfonyl)phenylthiomethyl]bicyclo[4.4.0]decane-2-carboxylate

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Technology Process of methyl 2-aza-3-methyl-4-(methoxymethoxy)-9-oxo-7-[(phenylsulfonyl)phenylthiomethyl]bicyclo[4.4.0]decane-2-carboxylate

There total 12 articles about methyl 2-aza-3-methyl-4-(methoxymethoxy)-9-oxo-7-[(phenylsulfonyl)phenylthiomethyl]bicyclo[4.4.0]decane-2-carboxylate 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: 78.0%

: 15296-86-3
1-(phenylsulfanyl)methyl phenyl sulfone

: 224184-02-5
methyl 2-aza-3-methyl-4-(methoxymethoxy)-9-oxobicyclo[4.4.0]dec-7-ene-2-carboxylate

: 224184-04-7
methyl 2-aza-3-methyl-4-(methoxymethoxy)-9-oxo-7-[(phenylsulfonyl)phenylthiomethyl]bicyclo[4.4.0]decane-2-carboxylate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 - -10 ℃;
DOI:10.1021/jo990141n

Reference yield:

: 165672-51-5
(5S,6S)-1-Benzyl-5-methoxymethoxy-6-methyl-piperidin-2-one

: 224184-04-7
methyl 2-aza-3-methyl-4-(methoxymethoxy)-9-oxo-7-[(phenylsulfonyl)phenylthiomethyl]bicyclo[4.4.0]decane-2-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1: 91 percent / NaH / liquid ammonia; tetrahydrofuran / 0.5 h / Heating

2: 77 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

3: 80 percent / LiHMDS / tetrahydrofuran / 0.5 h / -78 - -50 °C

4: 74 percent / Pd(PPh₃)4; Et₃N; Ph₃P / dimethylformamide / 1.5 h / 20 °C

5: 89 percent / MeLi; CuI / diethyl ether / -78 - -30 °C

6: 290 mg

7: LiOH*H₂O; H₂O / methanol / 1 h / 60 °C

8: 254 mg / 1,1'carbonyldiimidazole; Et₃N / CH₂Cl₂ / 16 h / 20 °C

9: 97 percent / tetrahydrofuran / 0.5 h / 0 - 20 °C

10: 84 percent / OsO₄; NaIO₄ / dioxane; H₂O / 1 h / 20 °C

11: 60 percent / DBU / benzene / 24 h / Heating

12: 78 percent / n-BuLi / tetrahydrofuran / -78 - -10 °C

With lithium hydroxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; water; methyllithium; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; ammonia; water; N,N-dimethyl-formamide; benzene; 1: Birch reduction / 2: Substitution / 3: Substitution / 4: Substitution / 5: Addition / 7: Hydrolysis / 8: Substitution / 9: Substitution / 10: Oxidation / 11: Cyclization / 12: Addition;
DOI:10.1016/S0040-4020(99)00603-1

Reference yield:

: 224183-76-0
methyl 6-methyl-5-(methoxymethoxy)-2-oxopiperidinecarboxylate

: 224184-04-7
methyl 2-aza-3-methyl-4-(methoxymethoxy)-9-oxo-7-[(phenylsulfonyl)phenylthiomethyl]bicyclo[4.4.0]decane-2-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 80 percent / LiHMDS / tetrahydrofuran / 0.5 h / -78 - -50 °C

2: 74 percent / Pd(PPh₃)4; Et₃N; Ph₃P / dimethylformamide / 1.5 h / 20 °C

3: 89 percent / MeLi; CuI / diethyl ether / -78 - -30 °C

4: 290 mg

5: LiOH*H₂O; H₂O / methanol / 1 h / 60 °C

6: 254 mg / 1,1'carbonyldiimidazole; Et₃N / CH₂Cl₂ / 16 h / 20 °C

7: 97 percent / tetrahydrofuran / 0.5 h / 0 - 20 °C

8: 84 percent / OsO₄; NaIO₄ / dioxane; H₂O / 1 h / 20 °C

9: 60 percent / DBU / benzene / 24 h / Heating

10: 78 percent / n-BuLi / tetrahydrofuran / -78 - -10 °C

With lithium hydroxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; water; methyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1: Substitution / 2: Substitution / 3: Addition / 5: Hydrolysis / 6: Substitution / 7: Substitution / 8: Oxidation / 9: Cyclization / 10: Addition;
DOI:10.1016/S0040-4020(99)00603-1