(S)-tert-butyl 3-[N-allyl-N-((R)-1-phenylethyl)amino]-3-phenylpropanoate

Base Information

• Chemical Name: (S)-tert-butyl 3-[N-allyl-N-((R)-1-phenylethyl)amino]-3-phenylpropanoate
• CAS No.: 1032169-20-2
• Molecular Formula: C₂₄H₃₁NO₂
• Molecular Weight: 365.516

Synonyms:(S)-tert-butyl 3-[N-allyl-N-((R)-1-phenylethyl)amino]-3-phenylpropanoate

Chemical Property of (S)-tert-butyl 3-[N-allyl-N-((R)-1-phenylethyl)amino]-3-phenylpropanoate

Chemical Property:

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Technology Process of (S)-tert-butyl 3-[N-allyl-N-((R)-1-phenylethyl)amino]-3-phenylpropanoate

There total 4 articles about (S)-tert-butyl 3-[N-allyl-N-((R)-1-phenylethyl)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: 87.0%

tert-butyl cinnamate (14990-09-1) + (R)-N-allyl (1-phenylethyl)amine (126275-19-2) → (S)-tert-butyl 3-[N-allyl-N-((R)-1-phenylethyl)amino]-3-phenylpropanoate (1032169-20-2)

Guidance literature:

(R)-N-allyl (1-phenylethyl)amine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

tert-butyl cinnamate; In tetrahydrofuran; hexane; at -78 ℃; for 1h; diastereoselective reaction;

DOI:10.1021/ol800722a

Reference yield:

2,2,6,6-tetramethylpiperidine-1-oxoammonium hexafluorophosphate (863309-36-8) + tert-butyl cinnamate (14990-09-1) + (R)-N-allyl (1-phenylethyl)amine (126275-19-2) → (S)-tert-butyl 3-[N-allyl-N-((R)-1-phenylethyl)amino]-3-phenylpropanoate (1032169-20-2) + (2S,3S,4R)-tert-butyl 2-phenyl-1-((R)-1-phenylethyl)-4-[(2,2,6,6-tetramethyl-piperidin-1-yloxy)methyl]pyrrolidine-3-carboxylate + (2S,3S,4S)-tert-butyl 2-phenyl-1-((R)-1-phenylethyl)-4-[(2,2,6,6-tetramethyl-piperidin-1-yloxy)methyl]pyrrolidine-3-carboxylate

Guidance literature:

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

tert-butyl cinnamate; In tetrahydrofuran; hexane; for 0.5h;

2,2,6,6-tetramethylpiperidine-1-oxoammonium hexafluorophosphate; With ferrocene; In tetrahydrofuran; hexane; at -78 ℃;

DOI:10.1002/anie.201403776

Reference yield:

(R)-1-phenyl-ethyl-amine (3886-69-9) → (S)-tert-butyl 3-[N-allyl-N-((R)-1-phenylethyl)amino]-3-phenylpropanoate (1032169-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

1.2: 4 h

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.5 h

2.3: -78 °C

With n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1002/anie.201403776

upstream raw materials:

tert-butyl cinnamate

(R)-N-allyl (1-phenylethyl)amine

2,2,6,6-tetramethylpiperidine-1-oxoammonium hexafluorophosphate

(R)-1-phenyl-ethyl-amine

Downstream raw materials:

tert-butyl (3S)-3-{(3-iodopropyl)[(R)-1-phenylethyl]amino}-3-phenylpropanoate

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