tert-butyl (3S,5S)-3-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-5-{[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]carbamoyl}piperidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (3S,5S)-3-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-5-{[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]carbamoyl}piperidine-1-carboxylate
CAS No.:1620523-77-4
Molecular Formula:C₃₅H₄₇FN₄O₄
Molecular Weight:606.781
Hs Code.:

tert-butyl (3S,5S)-3-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-5-{[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]carbamoyl}piperidine-1-carboxylate

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Chemical Property of tert-butyl (3S,5S)-3-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-5-{[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]carbamoyl}piperidine-1-carboxylate

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Technology Process of tert-butyl (3S,5S)-3-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-5-{[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]carbamoyl}piperidine-1-carboxylate

There total 10 articles about tert-butyl (3S,5S)-3-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-5-{[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]carbamoyl}piperidine-1-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: 100.0%

: (1R)-1-(5-fluoro-2-pyridyl)-3-methylbutan-1-amine dihydrochloride

: 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

: 1620523-77-4
tert-butyl (3S,5S)-3-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-5-{[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]carbamoyl}piperidine-1-carboxylate

Guidance literature:: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 1h; Cooling with ice;
DOI:10.3987/COM-14-12988

Reference yield:

: 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

: 1620523-77-4
tert-butyl (3S,5S)-3-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-5-{[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]carbamoyl}piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / Cooling with ice

With lithium hydroxide monohydrate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.3987/COM-14-12988

Reference yield:

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

: 1620523-77-4
tert-butyl (3S,5S)-3-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-5-{[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]carbamoyl}piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 10 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

10.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / Cooling with ice

With borane-THF; oxalyl dichloride; 18-crown-6 ether; lithium hydroxide monohydrate; ammonium chloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 2.1: |Swern Oxidation / 3.1: |Barbier Coupling Reaction;
DOI:10.3987/COM-14-12988