tert-butyl (3S,2'S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]propanoate

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Chemical Name:tert-butyl (3S,2'S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]propanoate
CAS No.:1418282-22-0
Molecular Formula:C₃₃H₄₂N₂O₂
Molecular Weight:498.709
Hs Code.:

Synonyms:tert-butyl (3S,2'S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]propanoate

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Chemical Property of tert-butyl (3S,2'S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]propanoate

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Technology Process of tert-butyl (3S,2'S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]propanoate

There total 4 articles about tert-butyl (3S,2'S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]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: 73.0%

: 1418282-18-4
tert-butyl (S,E)-3-[N(1')-benzylpyrrolidin-2'-yl]propenoate

: 38235-77-7
(R)-N-benzyl-1-phenylethylamine

: 1418282-22-0
tert-butyl (3S,2'S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]propanoate

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

tert-butyl (S,E)-3-[N(1')-benzylpyrrolidin-2'-yl]propenoate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1016/j.tet.2012.11.080

Reference yield:

: 147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7
L-proline

: 1418282-22-0
tert-butyl (3S,2'S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]propanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydroxide / water / 2 h / 0 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 17 h / 0 °C / Reflux

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0.5 h / -78 - 20 °C

4.2: 18 h / 20 °C

5.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

5.2: 2 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; sodium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water;
DOI:10.1016/j.tet.2012.11.080

Reference yield:

: 53912-80-4
(S)-N-benzylprolinol

: 1418282-22-0
tert-butyl (3S,2'S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]propanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0.5 h / -78 - 20 °C

2.2: 18 h / 20 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

3.2: 2 h / -78 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.tet.2012.11.080