1-tert-butyl 3-methyl (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-1,3-dicarboxylate

Base Information

Chemical Name:1-tert-butyl 3-methyl (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-1,3-dicarboxylate
CAS No.:1620523-75-2
Molecular Formula:C₂₆H₃₆N₂O₅
Molecular Weight:456.582
Hs Code.:

Synonyms:1-tert-butyl 3-methyl (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-1,3-dicarboxylate

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Chemical Property of 1-tert-butyl 3-methyl (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-1,3-dicarboxylate

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Technology Process of 1-tert-butyl 3-methyl (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-1,3-dicarboxylate

There total 8 articles about 1-tert-butyl 3-methyl (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-1,3-dicarboxylate 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: 72.0%

: 1620523-74-1
1-tert-butyl 3-methyl (3S,5R)-5-{3-[N-(2-diethoxyphosphorylacetyl)-2-methylanilino]-2,2-dimethylpropanoyl}piperidine-1,3-dicarboxylate

: 1620523-75-2
1-tert-butyl 3-methyl (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-1,3-dicarboxylate

Guidance literature:: 1-tert-butyl 3-methyl (3S,5R)-5-{3-[N-(2-diethoxyphosphorylacetyl)-2-methylanilino]-2,2-dimethylpropanoyl}piperidine-1,3-dicarboxylate; With 18-crown-6 ether; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - -20 ℃;
DOI:10.3987/COM-14-12988

Reference yield:

: 534572-20-8
(3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid

: 1620523-75-2
1-tert-butyl 3-methyl (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-1,3-dicarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: borane-THF / 1 h / -78 - 20 °C

2.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.75 h / -78 °C

2.2: 2 h / -78 - 0 °C

3.1: ammonium chloride; zinc / tetrahydrofuran / 1.5 h / 20 °C

4.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.83 h / -78 °C

4.2: 2 h / -78 - 0 °C

5.1: ozone / dichloromethane / 3 h / -78 °C / Inert atmosphere

5.2: 18 h / -78 - 4 °C

6.1: acetic acid / toluene / 1 h / 80 °C / Cooling with ice

6.2: 1.5 h / 20 °C

7.1: dichloromethane; N,N-dimethyl acetamide / 0 - 20 °C

8.1: 18-crown-6 ether / tetrahydrofuran; toluene / 0.5 h / -78 °C

8.2: -78 - -20 °C

With borane-THF; oxalyl dichloride; 18-crown-6 ether; ammonium chloride; ozone; acetic acid; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide; toluene; 2.1: |Swern Oxidation / 3.1: |Barbier Coupling Reaction;
DOI:10.3987/COM-14-12988

Reference yield:

: 1620523-71-8
1-tert-butyl 3-methyl (3S,5R)-5-(2,2-dimethylbut-3-enoyl)piperidine-1,3-dicarboxylate

: 1620523-75-2
1-tert-butyl 3-methyl (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-1,3-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: ozone / dichloromethane / 3 h / -78 °C / Inert atmosphere

1.2: 18 h / -78 - 4 °C

2.1: acetic acid / toluene / 1 h / 80 °C / Cooling with ice

2.2: 1.5 h / 20 °C

3.1: dichloromethane; N,N-dimethyl acetamide / 0 - 20 °C

4.1: 18-crown-6 ether / tetrahydrofuran; toluene / 0.5 h / -78 °C

4.2: -78 - -20 °C

With 18-crown-6 ether; ozone; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; toluene;
DOI:10.3987/COM-14-12988