(+)-(2R,6R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2,6-dimethylcyclohexan-1-one

Base Information

Chemical Name:(+)-(2R,6R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2,6-dimethylcyclohexan-1-one
CAS No.:334686-30-5
Molecular Formula:C₂₀H₂₉NO₄S
Molecular Weight:379.521
Hs Code.:

Synonyms:(+)-(2R,6R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2,6-dimethylcyclohexan-1-one

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Chemical Property of (+)-(2R,6R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2,6-dimethylcyclohexan-1-one

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Technology Process of (+)-(2R,6R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2,6-dimethylcyclohexan-1-one

There total 4 articles about (+)-(2R,6R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2,6-dimethylcyclohexan-1-one 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: 83.0%

: 334686-29-2
(-)-(2R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2-methylcyclohexan-1-one

: 74-88-4
methyl iodide

: 334686-30-5
(+)-(2R,6R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2,6-dimethylcyclohexan-1-one

: (-)-(2R,6S)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2,6-dimethylcyclohexan-1-one

Guidance literature:: (-)-(2R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2-methylcyclohexan-1-one; With 18-crown-6 ether; potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 - 20 ℃; for 15h; Further stages.;
DOI:10.1002/1099-0690(200102)2001:4<647::AID-EJOC647>3.0.CO;2-6

Reference yield:

: 79514-33-3
(S) (+)-N-tosyl-2-aminobutanol

: 334686-30-5
(+)-(2R,6R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2,6-dimethylcyclohexan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: MsOH / 3 h / 20 °C

1.2: 80 percent / K₂CO₃ / 0.17 h / 20 °C

2.1: ZnCl₂*Et₂O / CH₂Cl₂ / 0.25 h / 0 °C

3.1: LDA / tetrahydrofuran / 1 h / -78 °C

3.2: tetrahydrofuran / 15 h / 0 - 20 °C

With methanesulfonic acid; zinc chloride diethyl ether; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1002/1099-0690(200102)2001:4<647::AID-EJOC647>3.0.CO;2-6

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 334686-30-5
(+)-(2R,6R)-2-{(2S,4S)-4-ethyl-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidin-2-yl}-2,6-dimethylcyclohexan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: NEt₃ / CH₂Cl₂ / 18 h / 20 °C

2.1: MsOH / 3 h / 20 °C

2.2: 80 percent / K₂CO₃ / 0.17 h / 20 °C

3.1: ZnCl₂*Et₂O / CH₂Cl₂ / 0.25 h / 0 °C

4.1: LDA / tetrahydrofuran / 1 h / -78 °C

4.2: tetrahydrofuran / 15 h / 0 - 20 °C

With methanesulfonic acid; zinc chloride diethyl ether; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1002/1099-0690(200102)2001:4<647::AID-EJOC647>3.0.CO;2-6