tert-butyl 2-aza-3-methyl-4-(methoxymethoxy)-7-[(phenylsulfonyl)methyl]bicyclo[4.4.0]decane-2-carboxylate

Base Information

Chemical Name:tert-butyl 2-aza-3-methyl-4-(methoxymethoxy)-7-[(phenylsulfonyl)methyl]bicyclo[4.4.0]decane-2-carboxylate
CAS No.:224184-10-5
Molecular Formula:C₂₄H₃₇NO₆S
Molecular Weight:467.627
Hs Code.:

Synonyms:

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

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

There total 20 articles about tert-butyl 2-aza-3-methyl-4-(methoxymethoxy)-7-[(phenylsulfonyl)methyl]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:

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

: 224184-10-5
tert-butyl 2-aza-3-methyl-4-(methoxymethoxy)-7-[(phenylsulfonyl)methyl]bicyclo[4.4.0]decane-2-carboxylate

Guidance literature:: Multi-step reaction with 18 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

13: 85 percent / n-Bu₃SnH; AIBN / benzene / 2 h / Heating

14: NaBH₄ / CH₂Cl₂; methanol / 2 h / 0 °C

15: 1,2-dichloro-ethane / 7 h / Heating

16: 39 mg / AIBN; n-Bu₃SnH / toluene / 2 h / Heating

17: n-PrSH; n-BuLi / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 48 h / 20 °C

18: 115 mg / benzene / 2 h / Heating

With lithium hydroxide; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1-thiopropane; 2,2'-azobis(isobutyronitrile); water; methyllithium; tri-n-butyl-tin hydride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; ammonia; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene; 1: Birch reduction / 2: Substitution / 3: Substitution / 4: Substitution / 5: Addition / 7: Hydrolysis / 8: Substitution / 9: Substitution / 10: Oxidation / 11: Cyclization / 12: Addition / 13: Reduction / 14: Reduction / 15: Substitution / 16: Reduction / 17: Reduction / 18: Substitution;
DOI:10.1016/S0040-4020(99)00603-1

Reference yield:

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

: 224184-10-5
tert-butyl 2-aza-3-methyl-4-(methoxymethoxy)-7-[(phenylsulfonyl)methyl]bicyclo[4.4.0]decane-2-carboxylate

Guidance literature:: Multi-step reaction with 16 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

11: 85 percent / n-Bu₃SnH; AIBN / benzene / 2 h / Heating

12: NaBH₄ / CH₂Cl₂; methanol / 2 h / 0 °C

13: 1,2-dichloro-ethane / 7 h / Heating

14: 39 mg / AIBN; n-Bu₃SnH / toluene / 2 h / Heating

15: n-PrSH; n-BuLi / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 48 h / 20 °C

16: 115 mg / benzene / 2 h / Heating

With lithium hydroxide; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1-thiopropane; 2,2'-azobis(isobutyronitrile); water; methyllithium; tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene; 1: Substitution / 2: Substitution / 3: Addition / 5: Hydrolysis / 6: Substitution / 7: Substitution / 8: Oxidation / 9: Cyclization / 10: Addition / 11: Reduction / 12: Reduction / 13: Substitution / 14: Reduction / 15: Reduction / 16: Substitution;
DOI:10.1016/S0040-4020(99)00603-1

Reference yield:

: 224184-14-9
(5S,6S)-5-Methoxymethoxy-6-methyl-piperidin-2-one

: 224184-10-5
tert-butyl 2-aza-3-methyl-4-(methoxymethoxy)-7-[(phenylsulfonyl)methyl]bicyclo[4.4.0]decane-2-carboxylate

Guidance literature:: Multi-step reaction with 17 steps

1: 77 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

2: 80 percent / LiHMDS / tetrahydrofuran / 0.5 h / -78 - -50 °C

3: 74 percent / Pd(PPh₃)4; Et₃N; Ph₃P / dimethylformamide / 1.5 h / 20 °C

4: 89 percent / MeLi; CuI / diethyl ether / -78 - -30 °C

5: 290 mg

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

7: 254 mg / 1,1'carbonyldiimidazole; Et₃N / CH₂Cl₂ / 16 h / 20 °C

8: 97 percent / tetrahydrofuran / 0.5 h / 0 - 20 °C

9: 84 percent / OsO₄; NaIO₄ / dioxane; H₂O / 1 h / 20 °C

10: 60 percent / DBU / benzene / 24 h / Heating

11: 78 percent / n-BuLi / tetrahydrofuran / -78 - -10 °C

12: 85 percent / n-Bu₃SnH; AIBN / benzene / 2 h / Heating

13: NaBH₄ / CH₂Cl₂; methanol / 2 h / 0 °C

14: 1,2-dichloro-ethane / 7 h / Heating

15: 39 mg / AIBN; n-Bu₃SnH / toluene / 2 h / Heating

16: n-PrSH; n-BuLi / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 48 h / 20 °C

17: 115 mg / benzene / 2 h / Heating

With lithium hydroxide; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1-thiopropane; 2,2'-azobis(isobutyronitrile); water; methyllithium; tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene; 1: Substitution / 2: Substitution / 3: Substitution / 4: Addition / 6: Hydrolysis / 7: Substitution / 8: Substitution / 9: Oxidation / 10: Cyclization / 11: Addition / 12: Reduction / 13: Reduction / 14: Substitution / 15: Reduction / 16: Reduction / 17: Substitution;
DOI:10.1016/S0040-4020(99)00603-1