(2S,3S)-1-benzyl-2-methylpyrrolidin-3-amine

Base Information

• Chemical Name: (2S,3S)-1-benzyl-2-methylpyrrolidin-3-amine
• CAS No.: 202742-87-8
• Molecular Formula: C₁₂H₁₈N₂
• Molecular Weight: 190.288
• Mol file: 202742-87-8.mol

Synonyms:

Chemical Property of (2S,3S)-1-benzyl-2-methylpyrrolidin-3-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-1-benzyl-2-methylpyrrolidin-3-amine

There total 10 articles about (2S,3S)-1-benzyl-2-methylpyrrolidin-3-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:

(2S,3S)-3-azido-1-benzyl-2-methylpyrrolidine (1337862-77-7) → (2S,3S)-1-benzyl-2-methylpyrrolidin-3-amine (202742-87-8)

Guidance literature:

With hydrogen; In methanol; at 20 ℃; for 5h;

DOI:10.1016/j.tet.2011.07.049

Reference yield:

(S)-tert-butyl-N-(3-oxohex-5-en-2-yl)carbamate (1294446-91-5) → (2S,3S)-1-benzyl-2-methylpyrrolidin-3-amine (202742-87-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium tetrahydroborate / ethanol / 20 °C

2.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 0 - 20 °C

3.1: sodium periodate; ruthenium(III) trichloride hydrate / tetrachloromethane; water; acetonitrile / 16 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C

4.2: 0 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 0 °C

5.2: 2.5 h / 0 - 20 °C

6.1: methanol; thionyl chloride / 2 h / 0 - 20 °C

7.1: dimethylsulfide borane complex / tetrahydrofuran / 20 h / 0 - 20 °C

8.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

9.1: sodium azide / N,N-dimethyl-formamide / 36 h / 80 °C

10.1: hydrogen / methanol / 5 h / 20 °C

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; sodium periodate; thionyl chloride; sodium azide; ruthenium(III) trichloride hydrate; dimethylsulfide borane complex; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2011.07.049

Reference yield:

tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)hex-5-en-2-ylcarbamate (1337862-62-0) → (2S,3S)-1-benzyl-2-methylpyrrolidin-3-amine (202742-87-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium periodate; ruthenium(III) trichloride hydrate / tetrachloromethane; water; acetonitrile / 16 h / 20 °C

2.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C

2.2: 0 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0 °C

3.2: 2.5 h / 0 - 20 °C

4.1: methanol; thionyl chloride / 2 h / 0 - 20 °C

5.1: dimethylsulfide borane complex / tetrahydrofuran / 20 h / 0 - 20 °C

6.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

7.1: sodium azide / N,N-dimethyl-formamide / 36 h / 80 °C

8.1: hydrogen / methanol / 5 h / 20 °C

With methanol; dmap; sodium periodate; thionyl chloride; sodium azide; ruthenium(III) trichloride hydrate; dimethylsulfide borane complex; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2011.07.049

upstream raw materials:

(S)-tert-butyl-N-(3-oxohex-5-en-2-yl)carbamate

(2S,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidine-1-carboxylate

(4R,5S)-1-benzyl-4-(tert-butyldimethylsilyloxy)-5-methylpyrrolidin-2-one

(2S,3R)-1-benzyl-2-methylpyrrolidin-3-ol