prop-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

Base Information

• Chemical Name: prop-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate
• CAS No.: 1596359-22-6
• Molecular Formula: C₂₇H₂₉NO₂
• Molecular Weight: 399.533

Synonyms:prop-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

Chemical Property of prop-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

Chemical Property:

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Technology Process of prop-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

There total 3 articles about prop-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate 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: 79.0%

allyl alcohol (107-18-6) + tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate (265669-72-5) → prop-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate (1596359-22-6)

Guidance literature:

With thionyl chloride; at 0 - 50 ℃; for 3h; diastereoselective reaction; Inert atmosphere;

DOI:10.1039/c4ob00274a

Reference yield:

tert-butyl cinnamate (14990-09-1) → prop-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate (1596359-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2: thionyl chloride / 3 h / 0 - 50 °C / Inert atmosphere

With thionyl chloride; In tetrahydrofuran;

DOI:10.1039/c4ob00274a

Reference yield:

lithium N-benzyl-N-((S)-1-phenylethyl)amide → prop-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate (1596359-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2: thionyl chloride / 3 h / 0 - 50 °C / Inert atmosphere

With thionyl chloride; In tetrahydrofuran;

DOI:10.1039/c4ob00274a

upstream raw materials:

tert-butyl cinnamate

allyl alcohol

tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

Downstream raw materials:

C₂₇H₂₉NO₂

methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-(α-methyl-benzyl)-amino]-3-phenylpropanoate

(3S,4R,αS)-N(1)-(α-methylbenzyl)-3-(prop-2′-en-1′-yl)-4-phenylazetidin-2-one

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