tert-butyl (1R,2S,5S,αS)-2-hydroxy-5-(N-benzyl-N-(α-methylbenzyl)amino)cyclopentanoate

Base Information

Chemical Name:tert-butyl (1R,2S,5S,αS)-2-hydroxy-5-(N-benzyl-N-(α-methylbenzyl)amino)cyclopentanoate
CAS No.:852052-46-1
Molecular Formula:C₂₅H₃₃NO₃
Molecular Weight:395.542
Hs Code.:

Synonyms:tert-butyl (1R,2S,5S,αS)-2-hydroxy-5-(N-benzyl-N-(α-methylbenzyl)amino)cyclopentanoate

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Chemical Property of tert-butyl (1R,2S,5S,αS)-2-hydroxy-5-(N-benzyl-N-(α-methylbenzyl)amino)cyclopentanoate

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Technology Process of tert-butyl (1R,2S,5S,αS)-2-hydroxy-5-(N-benzyl-N-(α-methylbenzyl)amino)cyclopentanoate

There total 2 articles about tert-butyl (1R,2S,5S,αS)-2-hydroxy-5-(N-benzyl-N-(α-methylbenzyl)amino)cyclopentanoate 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: 66.0%

: 852052-44-9
(E)-6-oxo-hex-2-enoic acid tert-butyl ester

: 17480-69-2
(S)-N-benzyl-1-phenylethylamine

: 852052-45-0
tert-butyl (3S,αS)-3-(N-benzyl-(α-methylbenzyl)amino)-6-oxohexanoate

: 852052-46-1
tert-butyl (1R,2S,5S,αS)-2-hydroxy-5-(N-benzyl-N-(α-methylbenzyl)amino)cyclopentanoate

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

(E)-6-oxo-hex-2-enoic acid tert-butyl ester; In tetrahydrofuran; at -78 - -20 ℃; for 4h;
DOI:10.1039/b500223k

Reference yield:

: 852052-53-0
tert-butyl-(E)-6-hydroxyhex-2-enoate

: 852052-46-1
tert-butyl (1R,2S,5S,αS)-2-hydroxy-5-(N-benzyl-N-(α-methylbenzyl)amino)cyclopentanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 56 percent / PCC; NaOAc / dimethylsulfoxide / 2 h / 0 °C

2.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

2.2: 66 percent / tetrahydrofuran / 4 h / -78 - -20 °C

With n-butyllithium; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; dimethyl sulfoxide;
DOI:10.1039/b500223k