Cyclohexanecarboxylic acid, 3-(hydroxyimino)-2-methoxy-, methyl ester, (1S-cis)- (9CI)

Base Information

• Chemical Name: Cyclohexanecarboxylic acid, 3-(hydroxyimino)-2-methoxy-, methyl ester, (1S-cis)- (9CI)
• CAS No.: 159581-81-4
• Molecular Formula: C9H15 N O4
• Molecular Weight: 201.222
• Mol file: 159581-81-4.mol

Synonyms:Cyclohexanecarboxylic acid, 3-(hydroxyimino)-2-methoxy-, methyl ester, (1S-cis)- (9CI)

Chemical Property of Cyclohexanecarboxylic acid, 3-(hydroxyimino)-2-methoxy-, methyl ester, (1S-cis)- (9CI)

Chemical Property:

• Boiling Point: 308.0±42.0 °C(Predicted)
• PKA: 11.63±0.60(Predicted)
• PSA: 68.12000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 0.80470

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclohexanecarboxylic acid, 3-(hydroxyimino)-2-methoxy-, methyl ester, (1S-cis)- (9CI)

There total 7 articles about Cyclohexanecarboxylic acid, 3-(hydroxyimino)-2-methoxy-, methyl ester, (1S-cis)- (9CI) 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: 96.0%

methyl (1S,2S)-2-methoxy-3-oxo-1-cyclohexane carboxylate (159581-79-0) → methyl (1S,2S)-3-(N-hydroxylamino)-2-methoxycyclohexane carboxylate (159581-81-4)

Guidance literature:

With pyridine; hydroxylamine hydrochloride; In ethanol;

DOI:10.1021/jo951693i

Reference yield:

(1S,2R)-2-methoxy-3-cyclohexenyl-1-carboxylic acid (158252-23-4) → methyl (1S,2S)-3-(N-hydroxylamino)-2-methoxycyclohexane carboxylate (159581-81-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / NaHCO₃, KI, I₂ / H₂O

2: 99 percent / Bu₃SnH, AIBN / benzene

3: 70 percent / K₂CO₃

4: 99 percent / DMSO, TFAA, Et₃N / CH₂Cl₂

5: 96 percent / NH₂OH*HCl, pyridine / ethanol

With pyridine; 2,2'-azobis(isobutyronitrile); hydroxylamine hydrochloride; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; potassium iodide; In ethanol; dichloromethane; water; benzene;

DOI:10.1021/jo951693i

Reference yield:

acetic acid (6S)-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-(1R)-cyclohex-2-enyl ester (158195-43-8) → methyl (1S,2S)-3-(N-hydroxylamino)-2-methoxycyclohexane carboxylate (159581-81-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / LiOH*H₂O / tetrahydrofuran; H₂O / Ambient temperature

2: 1.) KOH, Bu₄NHSO₄, 2.) H₂O / 1.) THF

3: 85 percent / NaHCO₃, KI, I₂ / H₂O

4: 99 percent / Bu₃SnH, AIBN / benzene

5: 70 percent / K₂CO₃

6: 99 percent / DMSO, TFAA, Et₃N / CH₂Cl₂

7: 96 percent / NH₂OH*HCl, pyridine / ethanol

With pyridine; potassium hydroxide; lithium hydroxide; 2,2'-azobis(isobutyronitrile); hydroxylamine hydrochloride; water; iodine; tri-n-butyl-tin hydride; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; potassium iodide; In tetrahydrofuran; ethanol; dichloromethane; water; benzene;

DOI:10.1021/jo951693i

upstream raw materials:

methyl (1S,2S)-2-methoxy-3-oxo-1-cyclohexane carboxylate

(1S,5R,8S)-8-Methoxy-6-oxa-bicyclo[3.2.1]octan-7-one

(1S,2R)-2-methoxy-3-cyclohexenyl-1-carboxylic acid

(1S,4S,5S,8S)-4-Iodo-8-methoxy-6-oxa-bicyclo[3.2.1]octan-7-one

Refernces