(3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide

Base Information

• Chemical Name: (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide
• CAS No.: 646066-05-9
• Molecular Formula: C₁₆H₂₅NO₅
• Molecular Weight: 311.378
• Mol file: 646066-05-9.mol

Synonyms:(3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide

Chemical Property of (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide

There total 3 articles about (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide 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: 86.0%

Nitroethane (79-24-3) + 5-(R)-<(1R,2S,5R)-(-)-menthyloxy>-3-bromo-2(5H)-furanone (220972-39-4) → (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide (646066-05-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/S0957-4166(99)00378-X

Reference yield:

(-)-menthol (2216-51-5) → (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide (646066-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1: p-toluenesulfonic acid / toluene / 96 h / 60 °C

2: p-TsOH / toluene / 70 °C

3: 86 percent / DBU / tetrahydrofuran / 0.5 h / 0 °C

With toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; toluene; 1: Condensation / 2: epimerization / 3: Condensation;

DOI:10.1016/S0957-4166(99)00378-X

Reference yield:

5-(S)-<(1R,2S,5R)-(-)-menthyloxy>-3-bromo-2(5H)-furanone (220972-46-3) → (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide (646066-05-9)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / toluene / 70 °C

2: 86 percent / DBU / tetrahydrofuran / 0.5 h / 0 °C

With toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; toluene; 1: epimerization / 2: Condensation;

DOI:10.1016/S0957-4166(99)00378-X

upstream raw materials:

Nitroethane

5-(R)-<(1R,2S,5R)-(-)-menthyloxy>-3-bromo-2(5H)-furanone

(-)-menthol

5-(S)-<(1R,2S,5R)-(-)-menthyloxy>-3-bromo-2(5H)-furanone