N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2R)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyronitrile

Base Information

• Chemical Name: N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2R)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyronitrile
• CAS No.: 377779-92-5
• Molecular Formula: C₂₂H₂₅N₃O
• Molecular Weight: 347.46
• Mol file: 377779-92-5.mol

Synonyms:N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2R)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyronitrile

Chemical Property of N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2R)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyronitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2R)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyronitrile

There total 4 articles about N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2R)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyronitrile 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: 81.0%

2-methyl-2-(1-methylindol-3-yl)propionaldehyde (184434-21-7) + D-2-phenylglycinol (56613-80-0) + tri-n-butyltin cyanide (2179-92-2) → N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2R)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyronitrile (377779-92-5) + (2S)-2-{[(1R)-2-hydroxy-1-phenylethyl]amino}-3-methyl-3-(1-methyl-1H-indole-3-yl)butanenitrile (377779-91-4)

Guidance literature:

2-methyl-2-(1-methylindol-3-yl)propionaldehyde; D-2-phenylglycinol; With scandium tris(trifluoromethanesulfonate); In dichloromethane; at 20 ℃; for 1h;

tri-n-butyltin cyanide; In dichloromethane; at 0 - 20 ℃; Further stages.;

DOI:10.1021/jo0104882

Reference yield: 74.0%

2-methyl-2-(1-methylindol-3-yl)propionaldehyde (184434-21-7) + trimethylsilyl cyanide (7677-24-9) + D-2-phenylglycinol (56613-80-0) → N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2R)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyronitrile (377779-92-5) + (2S)-2-{[(1R)-2-hydroxy-1-phenylethyl]amino}-3-methyl-3-(1-methyl-1H-indole-3-yl)butanenitrile (377779-91-4)

Guidance literature:

In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ol016982+

Reference yield:

1-methylindole (603-76-9) → N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2R)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyronitrile (377779-92-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / SnCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

2: 100 percent / NaOH / aq. ethanol

3: CH₂Cl₂ / 4 h / 20 °C

With sodium hydroxide; tin(IV) chloride; In ethanol; dichloromethane;

DOI:10.1021/ol016982+

upstream raw materials:

2-methyl-2-(1-methylindol-3-yl)propionaldehyde

D-2-phenylglycinol

tri-n-butyltin cyanide

trimethylsilyl cyanide