(2R)-N-(3-(1,5-dioxaspiro[5.5]undecan-7-yl)propyl)-2-phenylbut-3-en-1-amine

Base Information

• Chemical Name: (2R)-N-(3-(1,5-dioxaspiro[5.5]undecan-7-yl)propyl)-2-phenylbut-3-en-1-amine
• CAS No.: 1217596-67-2
• Molecular Formula: C₂₂H₃₃NO₂
• Molecular Weight: 343.51
• Mol file: 1217596-67-2.mol

Synonyms:(2R)-N-(3-(1,5-dioxaspiro[5.5]undecan-7-yl)propyl)-2-phenylbut-3-en-1-amine

Chemical Property of (2R)-N-(3-(1,5-dioxaspiro[5.5]undecan-7-yl)propyl)-2-phenylbut-3-en-1-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-N-(3-(1,5-dioxaspiro[5.5]undecan-7-yl)propyl)-2-phenylbut-3-en-1-amine

There total 11 articles about (2R)-N-(3-(1,5-dioxaspiro[5.5]undecan-7-yl)propyl)-2-phenylbut-3-en-1-amine 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: 49.0%

N-((R)-2-phenylbut-3-enyl)-3-(1,5-dioxaspiro[5.5]undecan-7-yl)propanamide → (2R)-N-(3-(1,5-dioxaspiro[5.5]undecan-7-yl)propyl)-2-phenylbut-3-en-1-amine (1217596-67-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 22 ℃; for 22h; Inert atmosphere;

DOI:10.1021/jo4018099

Reference yield:

(S)-2-(1-phenylallyl)malonic acid (1311201-72-5) → (2R)-N-(3-(1,5-dioxaspiro[5.5]undecan-7-yl)propyl)-2-phenylbut-3-en-1-amine (1217596-67-2)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium hydroxide / methanol / 80 °C / Inert atmosphere

2: diphenylphosphoranyl azide; triethylamine / 85 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 0 - 22 °C / Inert atmosphere

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 21 h / 22 °C / Inert atmosphere

5: lithium aluminium tetrahydride / diethyl ether / 22 h / 0 - 22 °C / Inert atmosphere

With dmap; lithium aluminium tetrahydride; diphenylphosphoranyl azide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; potassium hydroxide; In methanol; diethyl ether; dichloromethane; 2: |Curtius Rearrangement;

DOI:10.1021/jo4018099

Reference yield:

(2R)-(2-phenylbut-3-enyl)carbamic acid tert-butylester (1217596-53-6) → (2R)-N-(3-(1,5-dioxaspiro[5.5]undecan-7-yl)propyl)-2-phenylbut-3-en-1-amine (1217596-67-2)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / dichloromethane / 0 - 22 °C / Inert atmosphere

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 21 h / 22 °C / Inert atmosphere

3: lithium aluminium tetrahydride / diethyl ether / 22 h / 0 - 22 °C / Inert atmosphere

With dmap; lithium aluminium tetrahydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In diethyl ether; dichloromethane;

DOI:10.1021/jo4018099

upstream raw materials:

(S)-2-(1-phenylallyl)malonic acid

(2R)-(2-phenylbut-3-enyl)carbamic acid tert-butylester

benzyl 3-(2-oxocyclohexyl)propanoate

cyclohexanone