5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2R-phenylpyrrolidin-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2R-phenylpyrrolidin-1-carboxylic acid tert-butyl ester
CAS No.:441794-75-8
Molecular Formula:C₂₅H₃₅NO₄
Molecular Weight:413.557
Hs Code.:

Synonyms:5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2R-phenylpyrrolidin-1-carboxylic acid tert-butyl ester

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Chemical Property of 5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2R-phenylpyrrolidin-1-carboxylic acid tert-butyl ester

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Technology Process of 5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2R-phenylpyrrolidin-1-carboxylic acid tert-butyl ester

There total 8 articles about 5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2R-phenylpyrrolidin-1-carboxylic acid tert-butyl ester 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: 80.0%

: 441794-74-7
5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-phenylpyrrolidin-1-carboxylic acid tert-butyl ester

: 441794-75-8
5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2R-phenylpyrrolidin-1-carboxylic acid tert-butyl ester

Guidance literature:: With phosphorus pentachloride; In dichloromethane; at -60 ℃; for 0.5h;
DOI:10.1021/jo011184i

Reference yield:

: (2S,3R,8aS)-2-Isopropyl-5,8-dioxo-3-phenyl-octahydro-indolizine-7-carboxylic acid benzyl ester

: 441794-75-8
5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2R-phenylpyrrolidin-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 570 mg / H₂ / Pd/C / methanol

2: 66 percent / L-Selectride / tetrahydrofuran / 1 h / -78 °C

3: HCl conc. / methanol / 72 h / Heating

4: 245 mg / DMAP; Et₃N / acetonitrile

5: 85 percent / LiHMDS / tetrahydrofuran / 1 h / -78 °C

6: 80 percent / PCl₅ / CH₂Cl₂ / 0.5 h / -60 °C

With hydrogenchloride; dmap; phosphorus pentachloride; hydrogen; L-Selectride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo011184i

Reference yield:

: 441794-70-3
1-(3-benzyloxycarbonylpropionyl)-4S-isopropyl-5R-phenylpyrrolidine-2S-carboxylic acid methyl ester

: 441794-75-8
5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2R-phenylpyrrolidin-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: sodium tert-pentoxide / tetrahydrofuran / -20 °C

2: 570 mg / H₂ / Pd/C / methanol

3: 66 percent / L-Selectride / tetrahydrofuran / 1 h / -78 °C

4: HCl conc. / methanol / 72 h / Heating

5: 245 mg / DMAP; Et₃N / acetonitrile

6: 85 percent / LiHMDS / tetrahydrofuran / 1 h / -78 °C

7: 80 percent / PCl₅ / CH₂Cl₂ / 0.5 h / -60 °C

With hydrogenchloride; dmap; phosphorus pentachloride; hydrogen; sodium tert-pentoxide; L-Selectride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1: Dieckmann cyclization;
DOI:10.1021/jo011184i