tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-fluorophenyl)propanoate

Base Information

• Chemical Name: tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-fluorophenyl)propanoate
• CAS No.: 277745-39-8
• Molecular Formula: C₂₈H₃₂FNO₂
• Molecular Weight: 433.566

Synonyms:tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-fluorophenyl)propanoate

Chemical Property of tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-fluorophenyl)propanoate

Chemical Property:

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SDS file from LookChem

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Technology Process of tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-fluorophenyl)propanoate

There total 2 articles about tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-fluorophenyl)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: 83.0%

(R)-N-benzyl-1-phenylethylamine (38235-77-7) + (E)-3-(3-fluorophenyl)acrylic acid tert-butyl ester (277745-38-7) → tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-fluorophenyl)propanoate (277745-39-8)

Guidance literature:

(R)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

(E)-3-(3-fluorophenyl)acrylic acid tert-butyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; hexane; water; at -78 - 20 ℃; optical yield given as %de; diastereoselective reaction; Saturated solution;

DOI:10.1016/j.tetasy.2012.07.001

Reference yield:

3-Fluorocinnamic acid (20595-30-6) → tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-fluorophenyl)propanoate (277745-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene / 4.5 h / 110 °C / Heating / reflux

2.1: n-butyllithium / tetrahydrofuran; hexanes / 0.17 h / -78 - 20 °C

2.2: 2 h

With n-butyllithium; In tetrahydrofuran; hexanes; toluene;

Reference yield: 93.0%

tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-fluorophenyl)propanoate (277745-39-8) → tert-butyl (S)-3-amino-3-(3'-fluorophenyl)propanoate (1393363-73-9,309757-71-9)

Guidance literature:

With Pd(OH)2/C (6% w/w); hydrogen; In methanol; at 20 ℃; for 24h; under 3800.26 Torr;

DOI:10.1016/j.tetasy.2012.07.001

upstream raw materials:

(R)-N-benzyl-1-phenylethylamine

(E)-3-(3-fluorophenyl)acrylic acid tert-butyl ester

3-Fluorocinnamic acid

Downstream raw materials:

(S)-3-amino-3-(3'-fluorophenyl)propanoic acid

tert-butyl (S)-3-amino-3-(3'-fluorophenyl)propanoate

(S)-(1-(3-fluorophenyl)-3-oxopropyl)-carbamic acid tert-butyl ester

C₃₀H₄₂FN₃O₅S

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