(1R,2R,3S,4S)-2-(acetoxymethyl)-3-(tosyloxymethyl)-7-azabicyclo[2.2.1]heptane hydrochloride

Base Information

Chemical Name:(1R,2R,3S,4S)-2-(acetoxymethyl)-3-(tosyloxymethyl)-7-azabicyclo[2.2.1]heptane hydrochloride
CAS No.:1318800-16-6
Molecular Formula:C₁₇H₂₃NO₅S*ClH
Molecular Weight:389.9
Hs Code.:

Synonyms:(1R,2R,3S,4S)-2-(acetoxymethyl)-3-(tosyloxymethyl)-7-azabicyclo[2.2.1]heptane hydrochloride

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Chemical Property of (1R,2R,3S,4S)-2-(acetoxymethyl)-3-(tosyloxymethyl)-7-azabicyclo[2.2.1]heptane hydrochloride

Chemical Property:

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Technology Process of (1R,2R,3S,4S)-2-(acetoxymethyl)-3-(tosyloxymethyl)-7-azabicyclo[2.2.1]heptane hydrochloride

There total 3 articles about (1R,2R,3S,4S)-2-(acetoxymethyl)-3-(tosyloxymethyl)-7-azabicyclo[2.2.1]heptane hydrochloride 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:

: 1318800-15-5
(1R,2R,3S,4S)-2-(acetoxymethyl)-3-(hydroxymethyl)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane

: 98-59-9
p-toluenesulfonyl chloride

: 1318800-16-6
(1R,2R,3S,4S)-2-(acetoxymethyl)-3-(tosyloxymethyl)-7-azabicyclo[2.2.1]heptane hydrochloride

Guidance literature:: (1R,2R,3S,4S)-2-(acetoxymethyl)-3-(hydroxymethyl)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane; p-toluenesulfonyl chloride; With triethylamine; In dichloromethane; at 20 ℃;

With hydrogenchloride; In 1,4-dioxane; water; at 20 ℃; for 2h;
DOI:10.1016/j.tetasy.2011.05.016

Reference yield:

: 378245-82-0
dimethyl 7-aza-N-tert-butoxycarbonylbicyclo[2.2.1]heptane-2-endo,3-endo-dicarboxylate

: 1318800-16-6
(1R,2R,3S,4S)-2-(acetoxymethyl)-3-(tosyloxymethyl)-7-azabicyclo[2.2.1]heptane hydrochloride

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

2.1: Candida antarctica lipase B / diethyl ether / 2 h / 20 °C / Enzymatic reaction

3.1: triethylamine / dichloromethane / 20 °C

3.2: 2 h / 20 °C

With Candida antarctica lipase B; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/j.tetasy.2011.05.016

Reference yield:

: 1318800-13-3
tert-butyl (2R,3S)-2,3-bis(hydroxymethyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate

: 1318800-16-6
(1R,2R,3S,4S)-2-(acetoxymethyl)-3-(tosyloxymethyl)-7-azabicyclo[2.2.1]heptane hydrochloride

Guidance literature:: Multi-step reaction with 2 steps

1.1: Candida antarctica lipase B / diethyl ether / 2 h / 20 °C / Enzymatic reaction

2.1: triethylamine / dichloromethane / 20 °C

2.2: 2 h / 20 °C

With Candida antarctica lipase B; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1016/j.tetasy.2011.05.016