(5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-methylenecyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate

Base Information

Chemical Name:(5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-methylenecyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate
CAS No.:173143-23-2
Molecular Formula:C₁₉H₃₁NO₅
Molecular Weight:353.459
Hs Code.:

Synonyms:(5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-methylenecyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate

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Chemical Property of (5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-methylenecyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate

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Technology Process of (5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-methylenecyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate

There total 6 articles about (5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-methylenecyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate 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: 91.0%

: 173143-22-1
(5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-oxocyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate

: 173143-23-2
(5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-methylenecyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate

Guidance literature:: In tetrahydrofuran; toluene; at -78 - 20 ℃;
DOI:10.1016/S0040-4020(98)00219-1

Reference yield:

: 126587-36-8
(4S)-1,1-dimethylethyl 4-<(Z)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate

: 173143-23-2
(5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-methylenecyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: aq. NaOH / tetrahydrofuran / 0 - 20 °C

2.1: 10.3 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 4-dimethylaminopyridine / CH₂Cl₂ / 20 °C

3.1: toluene / 72 h / 130 °C

3.2: NaOH / tetrahydrofuran; H₂O / 0 - 20 °C

4.1: 840 mg / methanol; diethyl ether

5.1: 91 percent / tetrahydrofuran; toluene / -78 - 20 °C

With dmap; sodium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1.1: Hydrolysis / 2.1: Esterification / 3.1: Diels-Alder reaction / 3.2: Hydrolysis / 4.1: Methylation / 5.1: Condensation;
DOI:10.1016/S0040-4020(98)00219-1

Reference yield:

: (S)-4-((Z)-2-Carboxy-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 173143-23-2
(5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-methylenecyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 10.3 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 4-dimethylaminopyridine / CH₂Cl₂ / 20 °C

2.1: toluene / 72 h / 130 °C

2.2: NaOH / tetrahydrofuran; H₂O / 0 - 20 °C

3.1: 840 mg / methanol; diethyl ether

4.1: 91 percent / tetrahydrofuran; toluene / -78 - 20 °C

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1.1: Esterification / 2.1: Diels-Alder reaction / 2.2: Hydrolysis / 3.1: Methylation / 4.1: Condensation;
DOI:10.1016/S0040-4020(98)00219-1