(2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone

Base Information

Chemical Name:(2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone
CAS No.:868528-90-9
Molecular Formula:C₂₁H₂₉ClN₂O₅
Molecular Weight:424.925
Hs Code.:

Synonyms:(2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone

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Chemical Property of (2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone

Chemical Property:

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Technology Process of (2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone

There total 4 articles about (2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone 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: 14.0%

: 868528-95-4
4-(N,N-bis(tert-butoxycarbonyl)amino)cyclohexanone

: 868528-86-3
bis(6-chloropyridin-3-yl)iodonium chloride

: 5-(N-(tert-butoxycarbonyl)amino)-2-hydroxycyclohex-1-enecarboxylic acid tert-butyl ester

: (2S,4R)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone

: 868528-90-9
(2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone

Guidance literature:: With n-butyllithium; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; at -45 ℃; for 4h;
DOI:10.1002/anie.200501745

Reference yield:

: 53939-30-3
5-bromo-2-chloropyridine

: 868528-90-9
(2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone

Guidance literature:: Multi-step reaction with 2 steps

1: 71 percent / ClCH=CHICl₂; BuLi / diethyl ether; hexane / 4 h / -78 - 20 °C

2: (R,R)-bis(α-methylbenzyl)amine hydrochloride; BuLi / tetrahydrofuran; dimethylformamide; hexane / 4 h / -45 °C

With n-butyllithium; 1-chloro-2-(dichloro-λ³-iodanyl)-ethene; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200501745

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 868528-90-9
(2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / DMAP / tetrahydrofuran / 2 h / Heating

2: (R,R)-bis(α-methylbenzyl)amine hydrochloride; BuLi / tetrahydrofuran; dimethylformamide; hexane / 4 h / -45 °C

With dmap; n-butyllithium; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200501745