tert-butyl N-benzyl (3R,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate

Base Information

• Chemical Name: tert-butyl N-benzyl (3R,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate
• CAS No.: 797038-64-3
• Molecular Formula: C₃₁H₃₈N₂O₂
• Molecular Weight: 470.655

Synonyms:tert-butyl N-benzyl (3R,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate

Chemical Property of tert-butyl N-benzyl (3R,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate

Chemical Property:

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Technology Process of tert-butyl N-benzyl (3R,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate

There total 2 articles about tert-butyl N-benzyl (3R,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate 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%

(S)-N-benzyl-1-phenylethylamine (17480-69-2) + tert-butyl 1-(phenylmethyl)-2,5-dihydropyrrole-3-carboxylate (698358-08-6) → tert-butyl N-benzyl (3R,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate (797038-64-3)

Guidance literature:

(S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

tert-butyl 1-(phenylmethyl)-2,5-dihydropyrrole-3-carboxylate; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1039/b407558g

Reference yield:

tert-butyl prop-2-ynoate (13831-03-3) → tert-butyl N-benzyl (3R,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate (797038-64-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / CH₃COOH / CH₂Cl₂ / 4 h / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 79 percent / tetrahydrofuran / 3 h / -78 °C

With n-butyllithium; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b407558g

Reference yield: 100.0%

tert-butyl N-benzyl (3R,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate (797038-64-3) → tert-butyl N-benzyl (3S,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate (797038-65-4)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; for 3h; Heating;

DOI:10.1039/b407558g

upstream raw materials:

(S)-N-benzyl-1-phenylethylamine

tert-butyl 1-(phenylmethyl)-2,5-dihydropyrrole-3-carboxylate

tert-butyl prop-2-ynoate

Downstream raw materials:

tert-butyl N-benzyl (3S,4R,αS)-4-(N'-benzyl-N'-α-methylbenzylamino)tetrahydropyrrole-3-carboxylate

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