(+)-9a-epi-stemoamide

Base Information

• Chemical Name: (+)-9a-epi-stemoamide
• CAS No.: 1191043-74-9
• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.272
• Mol file: 1191043-74-9.mol

Synonyms:

Chemical Property of (+)-9a-epi-stemoamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-9a-epi-stemoamide

There total 11 articles about (+)-9a-epi-stemoamide 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: 60.0%

(3aR,10aR,10bR)-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione (1191043-82-9) + methyl iodide (74-88-4) → (+)-9a-epi-stemoamide (1191043-74-9,794528-61-3)

Guidance literature:

(3aR,10aR,10bR)-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1055/s-0029-1217558

Reference yield:

C13H19N3O5 → (+)-9a-epi-stemoamide (1191043-74-9,794528-61-3) + (1S,3aR,10aS,10bR)-1-methyloctahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione (794528-61-3)

Guidance literature:

With sodium cyanoborohydride; acetic acid; trimethylphosphane; In tetrahydrofuran; acetonitrile; at 20 ℃; for 23h; Overall yield = 90 percent; Overall yield = 40 mg; Inert atmosphere;

DOI:10.1002/anie.202102614

Reference yield:

C8H13BrO → (+)-9a-epi-stemoamide (1191043-74-9,794528-61-3) + (1S,3aR,10aS,10bR)-1-methyloctahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione (794528-61-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere

1.2: 3 h / 0 °C / Inert atmosphere

2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

4.1: ethylaluminum dichloride / toluene / 0.02 h / 20 °C / Inert atmosphere

5.1: potassium carbonate / methanol / 0.67 h / 50 °C / Inert atmosphere

6.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 10 h / 20 °C / Inert atmosphere

7.1: selenium(IV) oxide / 1,4-dioxane / 1 h / 90 °C / Inert atmosphere; Microwave irradiation

8.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 1 h

9.1: sodium azide / N,N-dimethyl-formamide / 1 h / 85 °C / Inert atmosphere

10.1: trimethylphosphane; sodium cyanoborohydride; acetic acid / tetrahydrofuran; acetonitrile / 23 h / 20 °C / Inert atmosphere

With selenium(IV) oxide; sodium azide; Hoveyda-Grubbs catalyst second generation; di-n-butylboryl trifluoromethanesulfonate; palladium on activated charcoal; hydrogen; dihydrogen peroxide; ethylaluminum dichloride; sodium cyanoborohydride; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hydroxide; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/anie.202102614

upstream raw materials:

(3aR,10aR,10bR)-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione

methyl iodide