(3R,αS)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-formyl-phenyl)-propanoate

Base Information

• Chemical Name: (3R,αS)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-formyl-phenyl)-propanoate
• CAS No.: 425431-82-9
• Molecular Formula: C₂₉H₃₃NO₃
• Molecular Weight: 443.586
• Mol file: 425431-82-9.mol

Synonyms:(3R,αS)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-formyl-phenyl)-propanoate

Chemical Property of (3R,αS)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-formyl-phenyl)-propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,αS)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-formyl-phenyl)-propanoate

There total 4 articles about (3R,αS)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-formyl-phenyl)-propanoate 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%

(S)-N-benzyl-1-phenylethylamine (17480-69-2) + (E)-t-butyl 4-formylcinnamate (208036-26-4) → (3R,αS)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-formyl-phenyl)-propanoate (425431-82-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 12h;

DOI:10.1016/S0040-4020(02)00369-1

Reference yield: 81.0%

(E)-t-butyl 4-formylcinnamate (208036-26-4) + lithium N-benzyl-N-((S)-1-phenylethyl)amide → (3R,αS)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-formyl-phenyl)-propanoate (425431-82-9)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0957-4166(01)00544-4

Reference yield:

tert-Butyl acrylate (1663-39-4,25232-27-3) → (3R,αS)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(4-formyl-phenyl)-propanoate (425431-82-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / tri-o-tolyl phosphine; Pd(OAc)2; NEt₃ / Heating

2: 81 percent / n-butyllithium / tetrahydrofuran / 12 h / -78 °C

With palladium diacetate; n-butyllithium; triethylamine; tris-(o-tolyl)phosphine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(02)00369-1

upstream raw materials:

(E)-t-butyl 4-formylcinnamate

(S)-N-benzyl-1-phenylethylamine

tert-Butyl acrylate

4-bromo-benzaldehyde

Downstream raw materials:

(3R,αS,E)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-[4-(3-tert-butoxy-3-oxoprop-1-enyl)phenyl]propanoate

(3R,αS,3'S,α'R)-di-tert-butyl benzene-1,4-bis[3-(N-benzyl-N-α-methylbenzylamino)propanoate]

(3R,αS,3'R,α'S)-di-tert-butyl benzene-1,4-bis[3-(N-benzyl-N-α-methylbenzylamino)propanoate]