(1S,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol

Base Information

• Chemical Name: (1S,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol
• CAS No.: 868528-87-4
• Molecular Formula: C₂₁H₃₁ClN₂O₅
• Molecular Weight: 426.941
• Mol file: 868528-87-4.mol

Synonyms:(1S,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol

Chemical Property of (1S,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol

There total 6 articles about (1S,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol 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: 83.0%

(2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone (868528-90-9) → (1R,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol + (1S,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol (868528-87-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -98 - -60 ℃; for 2.5h;

DOI:10.1002/anie.200501745

Reference yield:

4-(N,N-bis(tert-butoxycarbonyl)amino)cyclohexanone (868528-95-4) → (1S,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol (868528-87-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 83 percent / NaBH₄ / methanol / 2.5 h / -98 - -60 °C

With sodium tetrahydroborate; n-butyllithium; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200501745

Reference yield:

bis(6-chloropyridin-3-yl)iodonium chloride (868528-86-3) → (1S,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol (868528-87-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 83 percent / NaBH₄ / methanol / 2.5 h / -98 - -60 °C

With sodium tetrahydroborate; n-butyllithium; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200501745

upstream raw materials:

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

4-(N,N-bis(tert-butoxycarbonyl)amino)cyclohexanone

bis(6-chloropyridin-3-yl)iodonium chloride

5-bromo-2-chloropyridine

Downstream raw materials:

(1S,2R,4S)-methanesulfonic acid 4-amino-2-(6-chloropyridin-3-yl)cyclohexyl ester

epibatidine

(1S,2R,4S)-methanesulfonic acid 4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexyl ester