methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate

Base Information

• Chemical Name: methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate
• CAS No.: 225089-42-9
• Molecular Formula: C₁₈H₂₅NO₄S
• Molecular Weight: 351.467

Synonyms:methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate

Chemical Property of methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate

Chemical Property:

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Technology Process of methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate

There total 6 articles about methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate 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:

N-p-tolylsulfonyl-9-azabicyclo<3.3.1>nonan-3-one (180406-57-9) → methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate (225089-42-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / (R)-<2-(4-methylpiperazinyl)-1-phenylethyl>(2,2-dimethylpropyl)amine, n-BuLi, hexamethylphosphortriamide / tetrahydrofuran; hexane / 1.) -100 deg C to room temperature, 1 h, 2.) -100 deg C, 40 min

2: 1.) Et₂Zn, 2.) n-Bu₄NF / 1.) CH₂Cl₂, hexane, room temperature, 1 h, 2.) THF, room temperature, 20 min

3: phenyliodine bistrifluoroacetate, trifluoromethanesulfonic acid / 0.08 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; diethylzinc; (R)-N-(2,2-dimethylpropyl)-1-phenyl-2-(4-methylpiperazinyl)ethylamine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(99)00073-3

Reference yield:

(1S,5R)-N-(p-tolylsulfonyl)-3-(trimethylsilyloxy)-9-azabicyclo<3.3.1>non-2-ene (180580-54-5) → methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate (225089-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Et₂Zn, 2.) n-Bu₄NF / 1.) CH₂Cl₂, hexane, room temperature, 1 h, 2.) THF, room temperature, 20 min

2: phenyliodine bistrifluoroacetate, trifluoromethanesulfonic acid / 0.08 h / Ambient temperature

With trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; diethylzinc; bis-[(trifluoroacetoxy)iodo]benzene;

DOI:10.1016/S0040-4020(99)00073-3

Reference yield:

9-azabicyclo<3.3.1>nonan-3-one hydrochloride (72761-60-5) → methyl (2S,6R)-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine-6-ethanoate (225089-42-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / Na₂CO₃ / H₂O; CH₂Cl₂ / 12 h / Ambient temperature

2: 63 percent / (R)-<2-(4-methylpiperazinyl)-1-phenylethyl>(2,2-dimethylpropyl)amine, n-BuLi, hexamethylphosphortriamide / tetrahydrofuran; hexane / 1.) -100 deg C to room temperature, 1 h, 2.) -100 deg C, 40 min

3: 1.) Et₂Zn, 2.) n-Bu₄NF / 1.) CH₂Cl₂, hexane, room temperature, 1 h, 2.) THF, room temperature, 20 min

4: phenyliodine bistrifluoroacetate, trifluoromethanesulfonic acid / 0.08 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; diethylzinc; sodium carbonate; (R)-N-(2,2-dimethylpropyl)-1-phenyl-2-(4-methylpiperazinyl)ethylamine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1016/S0040-4020(99)00073-3

upstream raw materials:

methanol

(1S,2S,3R,4R,6R)-4-hydroxy-3-methyl-N-(p-tolylsulfonyl)-10-azatricyclo<4.3.1.0^2,4>decane

9-azabicyclo<3.3.1>nonan-3-one hydrochloride

p-toluenesulfonyl chloride

Downstream raw materials:

(2S,6S)-6-Methyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine

(2S,6R)-6-formylmethyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine

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