benzyl (7S,8S,10R)-7-[(1,3-dioxoisoindolin-2-yl)methyl]-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

Base Information

Chemical Name:benzyl (7S,8S,10R)-7-[(1,3-dioxoisoindolin-2-yl)methyl]-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate
CAS No.:1419075-32-3
Molecular Formula:C₂₉H₃₄N₂O₆
Molecular Weight:506.599
Hs Code.:

Synonyms:benzyl (7S,8S,10R)-7-[(1,3-dioxoisoindolin-2-yl)methyl]-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

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Chemical Property of benzyl (7S,8S,10R)-7-[(1,3-dioxoisoindolin-2-yl)methyl]-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

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Technology Process of benzyl (7S,8S,10R)-7-[(1,3-dioxoisoindolin-2-yl)methyl]-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

There total 10 articles about benzyl (7S,8S,10R)-7-[(1,3-dioxoisoindolin-2-yl)methyl]-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-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: 80.0%

: 85-44-9
phthalic anhydride

: 1419075-30-1
benzyl (7S,8S,10R)-7-(aminomethyl)-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

: 1419075-32-3
benzyl (7S,8S,10R)-7-[(1,3-dioxoisoindolin-2-yl)methyl]-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

Guidance literature:: With triethylamine; In toluene; for 3h; Dean-Stark; Reflux;
DOI:10.1002/ejoc.201200919

Reference yield:

: 1350922-84-7
(R)-benzyl [1-(2-(2-aminoethyl)-1,3-dioxan-2-yl)propan-2-yl]carbamate

: 1419075-32-3
benzyl (7S,8S,10R)-7-[(1,3-dioxoisoindolin-2-yl)methyl]-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

1.2: 0.5 h / 0 - 20 °C

2.1: palladium 10% on activated carbon; ammonium formate / methanol / 3 h / Reflux

3.1: magnesium sulfate / dichloromethane / Reflux

3.2: 14 h / 40 °C

4.1: palladium 10% on activated carbon; ammonium formate / methanol / 2 h / Reflux

5.1: sodium carbonate / dichloromethane; water / 3 h / 20 °C

6.1: Amberlite IRA 401 / methanol

7.1: triethylamine / toluene / 3 h / Dean-Stark; Reflux

With dmap; palladium 10% on activated carbon; ammonium formate; sodium carbonate; magnesium sulfate; triethylamine; In methanol; dichloromethane; water; toluene; 3.1: |Mannich Aminomethylation;
DOI:10.1002/ejoc.201200919

Reference yield:

: (R)-benzyl [1-(2-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1,3-dioxan-2-yl)propan-2-yl]carbamate

: 1419075-32-3
benzyl (7S,8S,10R)-7-[(1,3-dioxoisoindolin-2-yl)methyl]-10-methyl-8-propyl-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: hydrazine hydrate / methanol / 2 h / Reflux

2.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

2.2: 0.5 h / 0 - 20 °C

3.1: palladium 10% on activated carbon; ammonium formate / methanol / 3 h / Reflux

4.1: magnesium sulfate / dichloromethane / Reflux

4.2: 14 h / 40 °C

5.1: palladium 10% on activated carbon; ammonium formate / methanol / 2 h / Reflux

6.1: sodium carbonate / dichloromethane; water / 3 h / 20 °C

7.1: Amberlite IRA 401 / methanol

8.1: triethylamine / toluene / 3 h / Dean-Stark; Reflux

With dmap; palladium 10% on activated carbon; ammonium formate; sodium carbonate; magnesium sulfate; hydrazine hydrate; triethylamine; In methanol; dichloromethane; water; toluene; 4.1: |Mannich Aminomethylation;
DOI:10.1002/ejoc.201200919