ethyl (1R,2R,3S,4S)-2-(tert-butoxycarbonylamino)-4-cyano-3-hydroxycyclohexanecarboxylate

Base Information

Chemical Name:ethyl (1R,2R,3S,4S)-2-(tert-butoxycarbonylamino)-4-cyano-3-hydroxycyclohexanecarboxylate
CAS No.:1378923-14-8
Molecular Formula:C₁₅H₂₄N₂O₅
Molecular Weight:312.366
Hs Code.:

Synonyms:ethyl (1R,2R,3S,4S)-2-(tert-butoxycarbonylamino)-4-cyano-3-hydroxycyclohexanecarboxylate

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Chemical Property of ethyl (1R,2R,3S,4S)-2-(tert-butoxycarbonylamino)-4-cyano-3-hydroxycyclohexanecarboxylate

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Technology Process of ethyl (1R,2R,3S,4S)-2-(tert-butoxycarbonylamino)-4-cyano-3-hydroxycyclohexanecarboxylate

There total 4 articles about ethyl (1R,2R,3S,4S)-2-(tert-butoxycarbonylamino)-4-cyano-3-hydroxycyclohexanecarboxylate 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: 59.0%

: 1378923-10-4
ethyl (1R,2R,3R,4S)-2-(tert-butoxycarbonylamino)-3,4-epoxycyclohexanecarboxylate

: 5804-85-3
diethylaluminium cyanide

: 1378923-14-8
ethyl (1R,2R,3S,4S)-2-(tert-butoxycarbonylamino)-4-cyano-3-hydroxycyclohexanecarboxylate

Guidance literature:: ethyl (1R,2R,3R,4S)-2-(tert-butoxycarbonylamino)-3,4-epoxycyclohexanecarboxylate; diethylaluminium cyanide; In toluene; at 20 ℃; for 15h;

With water; In toluene; regioselective reaction;
DOI:10.1016/j.tet.2011.12.065

Reference yield:

: 1201815-23-7
ethyl (1R,2S)-2-aminocyclohex-3-enecarboxylate hydrochloride

: 1378923-14-8
ethyl (1R,2R,3S,4S)-2-(tert-butoxycarbonylamino)-4-cyano-3-hydroxycyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 8 h / 0 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 °C

3: toluene / 15 h / 20 °C

With triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tet.2011.12.065

Reference yield:

: 1201815-24-8
ethyl (1R,2S)-2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylate

: 1378923-14-8
ethyl (1R,2R,3S,4S)-2-(tert-butoxycarbonylamino)-4-cyano-3-hydroxycyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 °C

2: toluene / 15 h / 20 °C

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene;
DOI:10.1016/j.tet.2011.12.065