(3S,5S)-1-tert-butoxycarbonyl-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-3-carboxylic acid

Base Information

Chemical Name:(3S,5S)-1-tert-butoxycarbonyl-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-3-carboxylic acid
CAS No.:1620523-76-3
Molecular Formula:C₂₅H₃₄N₂O₅
Molecular Weight:442.555
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

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

There total 8 articles about (3S,5S)-1-tert-butoxycarbonyl-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-3-carboxylic acid 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: 92.0%

: 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

: 1620523-76-3
(3S,5S)-1-tert-butoxycarbonyl-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-3-carboxylic acid

Guidance literature:: With lithium hydroxide monohydrate; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.3987/COM-14-12988

Reference yield:

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

: 1620523-76-3
(3S,5S)-1-tert-butoxycarbonyl-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 9 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

9.1: lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 0 °C

With borane-THF; oxalyl dichloride; 18-crown-6 ether; lithium hydroxide monohydrate; 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

: 1620523-76-3
(3S,5S)-1-tert-butoxycarbonyl-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 5 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

5.1: lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 0 °C

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