isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate

Base Information

Chemical Name:isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate
CAS No.:369593-38-4
Molecular Formula:C₂₃H₂₇ClFNO₂
Molecular Weight:403.924
Hs Code.:

Synonyms:isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate

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Chemical Property of isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate

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Technology Process of isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate

There total 7 articles about isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate 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: 84.0%

: 369593-37-3
isobutyl (3S,4R,5S)-1-benzyl-4-(4-fluorophenyl)-5-(hydroxymethyl)pyrrolidine-3-carboxylate

: 369593-38-4
isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate

Guidance literature:: isobutyl (3S,4R,5S)-1-benzyl-4-(4-fluorophenyl)-5-(hydroxymethyl)pyrrolidine-3-carboxylate; With methanesulfonyl chloride; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 1h;

With triethylamine; In 1,2-dichloro-ethane; for 48h; Heating;
DOI:10.1016/S0040-4039(01)01096-6

Reference yield:

: isobutyl (3S,7aR)-5-oxo-3-phenyl-6-(phenylseleno)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate

: 369593-38-4
isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: H₂O₂ / CH₂Cl₂ / 0.5 h / 0 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: copper iodide / tetrahydrofuran / 0.5 h / -25 °C

2.3: 97 percent / tetrahydrofuran / 2 h / -78 °C

3.1: 44 percent / borane*tetrahydrofuran / tetrahydrofuran / 1.5 h / 20 °C

4.1: methanesulfonyl chloride / 1,2-dichloro-ethane / 0.83 h / 0 °C

4.2: 84 percent / Et₃N / 1,2-dichloro-ethane / 36 h / Heating

With n-butyllithium; borane-THF; dihydrogen peroxide; methanesulfonyl chloride; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1002/1099-0690(200211)2002:21<3543::AID-EJOC3543>3.0.CO;2-0

Reference yield:

: 369593-36-2
isobutyl (3S,6S,7R,7aR)-7-(4-fluorophenyl)-3-phenyl-5-oxo-tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate

: 369593-38-4
isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 44 percent / borane*tetrahydrofuran / tetrahydrofuran / 1.5 h / 20 °C

2.1: methanesulfonyl chloride / 1,2-dichloro-ethane / 0.83 h / 0 °C

2.2: 84 percent / Et₃N / 1,2-dichloro-ethane / 36 h / Heating

With borane-THF; methanesulfonyl chloride; In tetrahydrofuran; 1,2-dichloro-ethane;
DOI:10.1002/1099-0690(200211)2002:21<3543::AID-EJOC3543>3.0.CO;2-0