(1R,6R)-6-tert-butoxycarbonylamino-cyclohex-3-ene carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,6R)-6-tert-butoxycarbonylamino-cyclohex-3-ene carboxylic acid methyl ester
• CAS No.: 323196-39-0
• Molecular Formula: C₁₃H₂₁NO₄
• Molecular Weight: 255.314

Synonyms:(1R,6R)-6-tert-butoxycarbonylamino-cyclohex-3-ene carboxylic acid methyl ester

Chemical Property of (1R,6R)-6-tert-butoxycarbonylamino-cyclohex-3-ene carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

98%,99%, ^*data from raw suppliers

methyl(1R,6R)-rel-6-{[(tert-butoxy)carbonyl]amino}cyclohex-3-ene-1-carboxylate 95%+ ^*data from reagent suppliers

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Technology Process of (1R,6R)-6-tert-butoxycarbonylamino-cyclohex-3-ene carboxylic acid methyl ester

There total 5 articles about (1R,6R)-6-tert-butoxycarbonylamino-cyclohex-3-ene carboxylic acid methyl 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: 74.0%

(1R,2R)-cyclohex-4-ene 1,2-dicarboxylic acid monomethyl ester (323196-38-9) + tert-butyl alcohol (75-65-0) → (1R,6R)-6-tert-butoxycarbonylamino-cyclohex-3-ene carboxylic acid methyl ester (323196-39-0)

Guidance literature:

With diphenyl-phosphinic acid; triethylamine;

DOI:10.1016/S0040-4039(00)01576-8

Reference yield:

C9H11NO3 + tert-butyl alcohol (75-65-0) → methyl (1S,2R)-2-(tert-butoxycarbonylamino)cyclohex-4-enecarboxylate (1321925-40-9) + (1R,6R)-6-tert-butoxycarbonylamino-cyclohex-3-ene carboxylic acid methyl ester (323196-39-0)

Guidance literature:

With copper(l) chloride; In toluene; Reflux;

DOI:10.1016/j.tet.2011.05.131

Reference yield:

(1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester (116733-43-8) → (1R,6R)-6-tert-butoxycarbonylamino-cyclohex-3-ene carboxylic acid methyl ester (323196-39-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / H₂O; H₂O₂; LiOH*H₂O / tetrahydrofuran / 18 h / 20 °C

2: 74 percent / DPPA; Et₃N

With lithium hydroxide; diphenyl-phosphinic acid; water; dihydrogen peroxide; triethylamine; In tetrahydrofuran; 1: Hydrolysis / 2: Curtius rearrangement;

DOI:10.1016/S0040-4039(00)01576-8

upstream raw materials:

(1R,2R)-cyclohex-4-ene 1,2-dicarboxylic acid monomethyl ester

tert-butyl alcohol

(1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester

Downstream raw materials:

methyl (1R,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexanecarboxylate

methyl (1R,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-(tert-butyldimethylsilanyloxy)cyclohexanecarboxylate

methyl (1R,2R,4R,5R)-4-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilanyloxy)cyclohexancarboxylate

(1R,6R)-6-tert-butoxycarbonylamino-cyclohex-3-ene carboxylic acid

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