(2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

Base Information

Chemical Name:(2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone
CAS No.:237406-09-6
Molecular Formula:C₁₅H₂₃NO₃
Molecular Weight:265.353
Hs Code.:

Synonyms:(2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

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Chemical Property of (2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

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Technology Process of (2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

There total 1 articles about (2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone 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:

: 115512-81-7
(S)-2-methoxy-1-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]-5-methylbenzene

: 237406-09-6
(2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

Guidance literature:: With ammonia; In tert-butyl alcohol; at -78 ℃;
DOI:10.1016/S0040-4039(97)00094-4

Reference yield:

: 237406-09-6
(2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

: 74-88-4
methyl iodide

: 115513-10-5
((S)-2-Methoxy-1,5-dimethyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

Guidance literature:: With n-butyllithium; Multistep reaction; 1.) THF, -78 deg C -> 25 deg C, then 0 deg C; 2.) THF, HMPA, -78 deg C;
DOI:10.1016/S0040-4039(97)00094-4

Reference yield:

: 237406-09-6
(2-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

: 188052-35-9
(1S,2R)-1-benzyl(oxy)-2-methyl-2-tert-butyldimethylsilyl(oxy)methyl-4-thiophenylmethyl-3-cyclohexene

Guidance literature:: Multi-step reaction with 12 steps

1: n-BuLi, HMPA / tetrahydrofuran; hexane / 1.5 h / -78 °C

2: 91 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature

3: 100 percent / NaBH₄, ZnCl₂ / tetrahydrofuran / 1 h / -60 - -15 °C

4: 63 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.) room temp., 24 h, 2.) reflux, 3 d

5: 90 percent / I₂ / tetrahydrofuran; H₂O / 18 h / Ambient temperature

6: 98 percent / DIBAL-H / CH₂Cl₂ / 1.) -10 deg C, 15 min, 2.) 0 deg C, 15 min

7: 99 percent / 1,5-diazabicyclo<5.4.0>undecene-5 / CH₂Cl₂ / 1 h / Ambient temperature

8: 94 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

9: Et₂NLi / diethyl ether / Heating

10: 95 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / Ambient temperature

11: 98 percent / SOCl₂, pyridine / diethyl ether / 0.05 h / 0 °C

12: 88 percent / tetrahydrofuran / 1.5 h / Ambient temperature

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; n-butyllithium; thionyl chloride; lithium diethylamide; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water;
DOI:10.1016/S0040-4020(99)00305-1