(R)-(+)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate

Base Information

• Chemical Name: (R)-(+)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate
• CAS No.: 1379586-24-9
• Molecular Formula: C₂₅H₂₆N₂O₄
• Molecular Weight: 418.492
• Mol file: 1379586-24-9.mol

Synonyms:(R)-(+)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate

Chemical Property of (R)-(+)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(+)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate

There total 6 articles about (R)-(+)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate 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:

(E)-benzyl 4-(benzyloxy)-but-2-enoylcarbamate (1379586-20-5) + aniline (62-53-3) → (S)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate + (R)-(+)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate (1379586-24-9)

Guidance literature:

With [(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]-diaquo-palladium(II) bis(triflate); In toluene; at 50 ℃; for 38h; optical yield given as %ee; Inert atmosphere;

DOI:10.1039/c2ob25122a

Reference yield:

2-Benzyloxyethanol (622-08-2,1201808-31-2) → (S)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate + (R)-(+)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate (1379586-24-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C / Inert atmosphere

1.2: 0.33 h / -78 °C / Inert atmosphere

2.1: dichloromethane / 16 h

3.1: [(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]-diaquo-palladium(II) bis(triflate) / toluene / 38 h / 50 °C / Inert atmosphere

With oxalyl dichloride; [(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]-diaquo-palladium(II) bis(triflate); dimethyl sulfoxide; In dichloromethane; toluene; 1.1: Swern oxidation / 1.2: Swern oxidation;

DOI:10.1039/c2ob25122a

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → (S)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate + (R)-(+)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate (1379586-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 16 h

2: [(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]-diaquo-palladium(II) bis(triflate) / toluene / 38 h / 50 °C / Inert atmosphere

With [(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]-diaquo-palladium(II) bis(triflate); In dichloromethane; toluene;

DOI:10.1039/c2ob25122a

upstream raw materials:

(2-(benzyloxycarbonylamino)-2-oxoethyl)triphenyl-phosphonium chloride

(E)-benzyl 4-(benzyloxy)-but-2-enoylcarbamate

aniline

2-Benzyloxyethanol

Downstream raw materials:

4-(benzyloxy)-3-(phenylamino)butanoic acid

(2R,4R)-(-)-(2-benzyloxymethyl-1,2,3,4-tetrahydroquinolin-4-yl)-carbamic acid methyl ester

(2R,4R)-(+)-methyl 2-(benzyloxymethyl)-1-methyl-1,2,3,4-tetrahydroquinolin-4-ylcarbamate

2-(benzyloxymethyl)-1-methyl-1,2,3,4-tetrahydroquinolin-4-amine