3-(R)-methyl-1-[2-oxo-3-(R)-(3,4-difluorophenyl)tetrahydro-2H-pyran-4(R)-ylmethyl]piperidine-3-carboxylic acid ethyl ester

Base Information

Chemical Name:3-(R)-methyl-1-[2-oxo-3-(R)-(3,4-difluorophenyl)tetrahydro-2H-pyran-4(R)-ylmethyl]piperidine-3-carboxylic acid ethyl ester
CAS No.:855316-62-0
Molecular Formula:C₂₁H₂₇F₂NO₄
Molecular Weight:395.446
Hs Code.:

Synonyms:3-(R)-methyl-1-[2-oxo-3-(R)-(3,4-difluorophenyl)tetrahydro-2H-pyran-4(R)-ylmethyl]piperidine-3-carboxylic acid ethyl ester

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Chemical Property of 3-(R)-methyl-1-[2-oxo-3-(R)-(3,4-difluorophenyl)tetrahydro-2H-pyran-4(R)-ylmethyl]piperidine-3-carboxylic acid ethyl ester

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Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 3-(R)-methyl-1-[2-oxo-3-(R)-(3,4-difluorophenyl)tetrahydro-2H-pyran-4(R)-ylmethyl]piperidine-3-carboxylic acid ethyl ester

There total 5 articles about 3-(R)-methyl-1-[2-oxo-3-(R)-(3,4-difluorophenyl)tetrahydro-2H-pyran-4(R)-ylmethyl]piperidine-3-carboxylic acid ethyl 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: 81.0%

: 1-{2-(R)-[(S)-(3,4-difluorophenyl)-3-{N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylcarbamoyl}methyl]-4-hydroxybutyl}-3-(R)-methylpiperidine-3-carboxylic acid ethyl ester

: 855316-62-0
3-(R)-methyl-1-[2-oxo-3-(R)-(3,4-difluorophenyl)tetrahydro-2H-pyran-4(R)-ylmethyl]piperidine-3-carboxylic acid ethyl ester

Guidance literature:: 1-{2-(R)-[(S)-(3,4-difluorophenyl)-3-{N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylcarbamoyl}methyl]-4-hydroxybutyl}-3-(R)-methylpiperidine-3-carboxylic acid ethyl ester; With acetic acid; In toluene; at 60 ℃; for 120h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene;
DOI:10.1021/jo0504161

Reference yield:

: 658-93-5
(3,4-difluorophenyl)acetic acid

: 855316-62-0
3-(R)-methyl-1-[2-oxo-3-(R)-(3,4-difluorophenyl)tetrahydro-2H-pyran-4(R)-ylmethyl]piperidine-3-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / 2-hydroxypyridine N-oxide; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / H₂O; tetrahydrofuran / 20 °C

2.1: LiHMDS; LiCl / tetrahydrofuran / 0.5 h / 0 °C

2.2: tetrahydrofuran / 0.5 h / -20 °C

3.1: 79 percent / LiB(sec-Bu)3H / tetrahydrofuran / 2 h / -21 °C

4.1: acetic acid / toluene / 120 h / 60 °C

4.2: 81 percent / DBU

With 2-hydroxy-pyridine N-oxide; L-Selectride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; water; toluene; 2.2: Michael addition;
DOI:10.1021/jo0504161

Reference yield:

: 440370-39-8
(E)-1-(3-ethoxycarbonylallyl)-3-(R)-methylpiperidine-3-carboxylic acid ethyl ester

: 855316-62-0
3-(R)-methyl-1-[2-oxo-3-(R)-(3,4-difluorophenyl)tetrahydro-2H-pyran-4(R)-ylmethyl]piperidine-3-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: LiHMDS; LiCl / tetrahydrofuran / 0.5 h / 0 °C

1.2: tetrahydrofuran / 0.5 h / -20 °C

2.1: 79 percent / LiB(sec-Bu)3H / tetrahydrofuran / 2 h / -21 °C

3.1: acetic acid / toluene / 120 h / 60 °C

3.2: 81 percent / DBU

With L-Selectride; acetic acid; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; toluene; 1.2: Michael addition;
DOI:10.1021/jo0504161