(1R,2R)-1-<methyl>-2-carboxycyclopropane

Base Information

• Chemical Name: (1R,2R)-1-<methyl>-2-carboxycyclopropane
• CAS No.: 153861-53-1
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.249
• Mol file: 153861-53-1.mol

Synonyms:

Chemical Property of (1R,2R)-1-<methyl>-2-carboxycyclopropane

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-1-<methyl>-2-carboxycyclopropane

There total 16 articles about (1R,2R)-1-<methyl>-2-carboxycyclopropane 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: 84.0%

N-tert-butoxycarbonyl[(1S,2S)-2-(aminomethyl)cyclopropyl]methanol (1262755-28-1,167255-48-3,167255-49-4) → (1R,2R)-1-<methyl>-2-carboxycyclopropane (153861-53-1,1638768-80-5)

Guidance literature:

N-tert-butoxycarbonyl[(1S,2S)-2-(aminomethyl)cyclopropyl]methanol; With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;

With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 13h;

DOI:10.1016/j.bmc.2013.06.063

Reference yield: 82.0%

((1R,2R)-2-Hydroxymethyl-cyclopropylmethyl)-carbamic acid tert-butyl ester (167255-48-3,167255-49-4) → (1R,2R)-1-<methyl>-2-carboxycyclopropane (153861-53-1,1638768-80-5)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; at 0 ℃;

DOI:10.1021/jo00080a017

Reference yield:

(1R,2R)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(hydroxymethyl)cyclopropane (154001-59-9) → (1R,2R)-1-<methyl>-2-carboxycyclopropane (153861-53-1,1638768-80-5)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / dichloromethane / 2 h / 0 °C

2: sodium azide / N,N-dimethyl-formamide / 2 h / 60 °C

3: water; tin(ll) chloride / 1,4-dioxane / 12 h / Ambient temperature

4: sodium hydrogencarbonate / tetrahydrofuran; 1,4-dioxane / 3 h / Ambient temperature

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

6: chromium(VI) oxide; sulfuric acid / 0 °C

With chromium(VI) oxide; sodium azide; sulfuric acid; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; triethylamine; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00080a017

upstream raw materials:

((1R,2R)-2-Hydroxymethyl-cyclopropylmethyl)-carbamic acid tert-butyl ester

(1R,2R)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(hydroxymethyl)cyclopropane

(2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methanamine

(1R,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane