(+)-(1S,2R)-2-(hydroxy)-5-cyclohexenecarboxylic acid (N-methoxy-N-methyl)amide

Base Information

Chemical Name:(+)-(1S,2R)-2-(hydroxy)-5-cyclohexenecarboxylic acid (N-methoxy-N-methyl)amide
CAS No.:934831-80-8
Molecular Formula:C₉H₁₅NO₃
Molecular Weight:185.223
Hs Code.:

Synonyms:(+)-(1S,2R)-2-(hydroxy)-5-cyclohexenecarboxylic acid (N-methoxy-N-methyl)amide

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Chemical Property of (+)-(1S,2R)-2-(hydroxy)-5-cyclohexenecarboxylic acid (N-methoxy-N-methyl)amide

Chemical Property:

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Technology Process of (+)-(1S,2R)-2-(hydroxy)-5-cyclohexenecarboxylic acid (N-methoxy-N-methyl)amide

There total 4 articles about (+)-(1S,2R)-2-(hydroxy)-5-cyclohexenecarboxylic acid (N-methoxy-N-methyl)amide 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: 77.0%

: 934831-75-1
(+)-(1S,2R)-2-hydroxy-5-cyclohexenecarboxylic acid

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 934831-80-8
(+)-(1S,2R)-2-(hydroxy)-5-cyclohexenecarboxylic acid (N-methoxy-N-methyl)amide

Guidance literature:: With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1016/j.tetasy.2006.12.018

Reference yield:

: 934831-73-9
(+)-(2S)-N-[(2S,3R)-2-(ethenyl)-3-(hydroxy)-6-heptenoyl]bornane-10,2-sultam

: 934831-80-8
(+)-(1S,2R)-2-(hydroxy)-5-cyclohexenecarboxylic acid (N-methoxy-N-methyl)amide

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / Grubbs catalyst / CH₂Cl₂ / 24 h / 20 °C

2: 82 percent / hydrogen peroxide; lithium hydroxide / tetrahydrofuran; H₂O / 0 - 20 °C

3: 77 percent / N-methylmorpholine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 2 h / 0 °C

With 4-methyl-morpholine; lithium hydroxide; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tetasy.2006.12.018

Reference yield:

: 2100-17-6
4-pentenal

: 934831-80-8
(+)-(1S,2R)-2-(hydroxy)-5-cyclohexenecarboxylic acid (N-methoxy-N-methyl)amide

Guidance literature:: Multi-step reaction with 4 steps

1.1: triflic acid; triethylborane; ethyldiisopropylamine / CH₂Cl₂ / cooling

1.2: 87 percent / CH₂Cl₂ / cooling

2.1: 88 percent / Grubbs catalyst / CH₂Cl₂ / 24 h / 20 °C

3.1: 82 percent / hydrogen peroxide; lithium hydroxide / tetrahydrofuran; H₂O / 0 - 20 °C

4.1: 77 percent / N-methylmorpholine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 2 h / 0 °C

With 4-methyl-morpholine; lithium hydroxide; triethyl borane; trifluorormethanesulfonic acid; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tetasy.2006.12.018