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

Base Information

• Chemical Name: (1S,2R,4S)-methanesulfonic acid 4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexyl ester
• CAS No.: 868528-88-5
• Molecular Formula: C₂₂H₃₃ClN₂O₇S
• Molecular Weight: 505.032
• Mol file: 868528-88-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (1S,2R,4S)-methanesulfonic acid 4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexyl ester 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:

(1S,2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanol (868528-87-4) + methanesulfonyl chloride (124-63-0) → (1S,2R,4S)-methanesulfonic acid 4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexyl ester (868528-88-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1002/anie.200501745

Reference yield:

4-(N,N-bis(tert-butoxycarbonyl)amino)cyclohexanone (868528-95-4) → (1S,2R,4S)-methanesulfonic acid 4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexyl ester (868528-88-5)

Guidance literature:

Multi-step reaction with 3 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

3: Et₃N / CH₂Cl₂ / 4 h / 20 °C

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

DOI:10.1002/anie.200501745

Reference yield:

(2R,4S)-4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexanone (868528-90-9) → (1S,2R,4S)-methanesulfonic acid 4-(N,N-bis(tert-butoxycarbonyl)amino)-2-(6-chloropyridin-3-yl)cyclohexyl ester (868528-88-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / NaBH₄ / methanol / 2.5 h / -98 - -60 °C

2: Et₃N / CH₂Cl₂ / 4 h / 20 °C

With sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

DOI:10.1002/anie.200501745

upstream raw materials:

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

methanesulfonyl chloride

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

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

Downstream raw materials:

epibatidine

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