t-butyl 3-(N,N-diallylamino)-3-phenylpropionate

Base Information

• Chemical Name: t-butyl 3-(N,N-diallylamino)-3-phenylpropionate
• CAS No.: 282092-07-3
• Molecular Formula: C₁₉H₂₇NO₂
• Molecular Weight: 301.429

Synonyms:t-butyl 3-(N,N-diallylamino)-3-phenylpropionate

Chemical Property of t-butyl 3-(N,N-diallylamino)-3-phenylpropionate

Chemical Property:

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Technology Process of t-butyl 3-(N,N-diallylamino)-3-phenylpropionate

There total 1 articles about t-butyl 3-(N,N-diallylamino)-3-phenylpropionate 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: 89.0%

tert-butyl cinnamate (14990-09-1) + C6H10N(1-)*Li(1+) → t-butyl 3-(N,N-diallylamino)-3-phenylpropionate (282092-07-3)

Guidance literature:

C₆H₁₀N^(1-)*Li⁽¹⁺⁾; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

tert-butyl cinnamate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With ammonium chloride; In tetrahydrofuran; hexane; Further stages.;

DOI:10.1021/ja000565v

Reference yield: 3.0%

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) + t-butyl 3-(N,N-diallylamino)-3-phenylpropionate (282092-07-3) → t-butyl 1-allyl-4-[(2,2,6,6-tetramethylpiperidin-1-yloxy)methyl]-2-phenylpyrrolidin-3-carboxylate + t-butyl 1-allyl-4-[(2,2,6,6-tetramethylpiperidin-1-yloxy)methyl]-2-phenylpyrrolidin-3-carboxylate + t-butyl 3-(N,N-diallylamino)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)-3-phenylpropionate

Guidance literature:

t-butyl 3-(N,N-diallylamino)-3-phenylpropionate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - -60 ℃; for 1h;

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; With ferrocenium hexafluorophosphate; In tetrahydrofuran; hexane; at -78 - -60 ℃; for 2h;

DOI:10.1021/ja000565v

Reference yield:

t-butyl 3-(N,N-diallylamino)-3-phenylpropionate (282092-07-3) → N-allyl-4-phenylhexahydrofuro[3,4-c]pyrrol-1-one

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisopropylamine; BuLi / tetrahydrofuran; hexane / 1 h / -78 - -60 °C

1.2: ferrocenium hexafluorophosphate / tetrahydrofuran; hexane / 2 h / -78 - -60 °C

2.1: 83 percent / Zn; acetic acid; H₂O / tetrahydrofuran / 0.5 h / 50 °C

3.1: 98 percent / potassium t-butoxide / tetrahydrofuran / 1.5 h / -78 °C

With n-butyllithium; potassium tert-butylate; water; acetic acid; diisopropylamine; zinc; In tetrahydrofuran; hexane; 1.1: Metallation / 1.2: radical cyclization / 2.1: Hydrolysis / 3.1: Elimination;

DOI:10.1021/ja000565v

upstream raw materials:

tert-butyl cinnamate

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