N-Methyl-2'-<2-cyanoethyl)-thio>-2α-<(Z)-6-<(methyl-sulfonyl)oxy>-3-methyl-3-hexenyl>-3,3-dimethylcyclobutane-1α-carboxanilide

Base Information

Chemical Name:N-Methyl-2'-<2-cyanoethyl)-thio>-2α-<(Z)-6-<(methyl-sulfonyl)oxy>-3-methyl-3-hexenyl>-3,3-dimethylcyclobutane-1α-carboxanilide
CAS No.:81521-07-5
Molecular Formula:C₂₅H₃₆N₂O₄S₂
Molecular Weight:492.704
Hs Code.:

Synonyms:N-Methyl-2'-<2-cyanoethyl)-thio>-2α-<(Z)-6-<(methyl-sulfonyl)oxy>-3-methyl-3-hexenyl>-3,3-dimethylcyclobutane-1α-carboxanilide

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Chemical Property of N-Methyl-2'-<2-cyanoethyl)-thio>-2α-<(Z)-6-<(methyl-sulfonyl)oxy>-3-methyl-3-hexenyl>-3,3-dimethylcyclobutane-1α-carboxanilide

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Technology Process of N-Methyl-2'-<2-cyanoethyl)-thio>-2α-<(Z)-6-<(methyl-sulfonyl)oxy>-3-methyl-3-hexenyl>-3,3-dimethylcyclobutane-1α-carboxanilide

There total 30 articles about N-Methyl-2'-<2-cyanoethyl)-thio>-2α-<(Z)-6-<(methyl-sulfonyl)oxy>-3-methyl-3-hexenyl>-3,3-dimethylcyclobutane-1α-carboxanilide 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%

: 90191-50-7
N-Methyl-2'-<(2-cyanoethyl)thio>-2α-<(Z)-6-hydroxy-3-methyl-3-hexenyl>-3,3-dimethylcyclobutane-1α-carboxanilide

: 124-63-0
methanesulfonyl chloride

: 81521-07-5
N-Methyl-2'-<2-cyanoethyl)-thio>-2α-<(Z)-6-<(methyl-sulfonyl)oxy>-3-methyl-3-hexenyl>-3,3-dimethylcyclobutane-1α-carboxanilide

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo00187a006

Reference yield:

: 81491-35-2,90191-50-7,90191-51-8
(1R,2S)-2-((E)-6-Hydroxy-3-methyl-hex-3-enyl)-3,3-dimethyl-cyclobutanecarboxylic acid [2-(2-cyano-ethylsulfanyl)-phenyl]-methyl-amide

: 124-63-0
methanesulfonyl chloride

: 81491-36-3,81521-06-4,81521-07-5
N-Methyl-2'-<(2-cyanoethyl)thio>-2α-<(E)-6-<(methylsulfonyl)oxy>-3-methyl-3-hexenyl>-3,3-dimethylcyclobutane-1β-carboxanilide

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Yield given;
DOI:10.1021/jo00187a006

Reference yield:

: 37676-91-8
methyl (3,3-dimethyl-1-cyclobutene)carboxylate

: 81491-36-3,81521-06-4,81521-07-5
N-Methyl-2'-<(2-cyanoethyl)thio>-2α-<(E)-6-<(methylsulfonyl)oxy>-3-methyl-3-hexenyl>-3,3-dimethylcyclobutane-1β-carboxanilide

Guidance literature:: Multi-step reaction with 15 steps

1: 357 mg / potassium tert-butoxide / tetrahydrofuran; dimethylsulfoxide / 144 h / Ambient temperature

2: 2percent KOH / H₂O; ethanol / 1.)1 h, r.t., 2.)2 h, reflux

3: pyridine / 2 h / Heating

4: K₂CO₃ / acetone / 12 h / Heating

5: 1.33 g / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

6: 1.65 g / Imidazol / dimethylformamide / Ambient temperature

7: 99.5 percent / n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.)-78 deg C, 2 h, 2.)1 h, ice-salt bath

8: 446 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

9: 84.2 percent / sodium amalgam, anh. sodium hydrogen phosphate / methanol / 1.)0 deg C, 2.)R_.T_.

10: 390 mg / Jones reagent / acetone / 0.5 h / 0 °C

11: Oxalyl chloride / benzene / 1.)30 min., r.t., 2.)2 h, 60-65 deg C

12: 550 mg / K₂CO₃ / tetrahydrofuran / 1.5 h / 0 °C

13: Dimethylsulfide, boron trifluoride etherate / CH₂Cl₂ / 0.67 h / 0 °C

14: K₂CO₃ / methanol / 1 h / 0 °C

15: Triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; jones reagent; oxalyl dichloride; dimethylsulfide; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo00187a006