(2R,3'S)-1'-(3-phenylprop-2-ynoyl)-[2,3']bipiperidinyl-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2R,3'S)-1'-(3-phenylprop-2-ynoyl)-[2,3']bipiperidinyl-1-carboxylic acid tert-butyl ester
CAS No.:517907-26-5
Molecular Formula:C₂₄H₃₂N₂O₃
Molecular Weight:396.53
Hs Code.:

Synonyms:(2R,3'S)-1'-(3-phenylprop-2-ynoyl)-[2,3']bipiperidinyl-1-carboxylic acid tert-butyl ester

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Chemical Property of (2R,3'S)-1'-(3-phenylprop-2-ynoyl)-[2,3']bipiperidinyl-1-carboxylic acid tert-butyl ester

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Technology Process of (2R,3'S)-1'-(3-phenylprop-2-ynoyl)-[2,3']bipiperidinyl-1-carboxylic acid tert-butyl ester

There total 11 articles about (2R,3'S)-1'-(3-phenylprop-2-ynoyl)-[2,3']bipiperidinyl-1-carboxylic acid tert-butyl 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:

: 517907-37-8
allyl-((1R,2R)-2-hydroxymethylcyclopent-3-enyl)-carbamic acid tert-butyl ester

: 517907-26-5
(2R,3'S)-1'-(3-phenylprop-2-ynoyl)-[2,3']bipiperidinyl-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 3.5 h / 0 - 20 °C

2: 82 percent / (IHMes)(Cy₃P)Cl₂Ru=CHPh / CH₂Cl₂ / 2 h / Heating

3: 80 percent / potassium carbonate; thiophenol / dimethylformamide / 1 h / 70 °C

4: hydrogen / 10 percent Pd/C / ethanol / 15 h / 20 °C

5: 801 mg / potassium carbonate / tetrahydrofuran / 2 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; di-isopropyl azodicarboxylate; hydrogen; potassium carbonate; thiophenol; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Mitsunobu reaction;
DOI:10.1021/jo026803h

Reference yield:

: allyl-((1R,4R)-4-tributylstannanylmethoxy-cyclopent-2-enyl)-carbamic acid tert-butyl ester

: 517907-26-5
(2R,3'S)-1'-(3-phenylprop-2-ynoyl)-[2,3']bipiperidinyl-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 69 percent / n-BuLi / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

2: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 3.5 h / 0 - 20 °C

3: 82 percent / (IHMes)(Cy₃P)Cl₂Ru=CHPh / CH₂Cl₂ / 2 h / Heating

4: 80 percent / potassium carbonate; thiophenol / dimethylformamide / 1 h / 70 °C

5: hydrogen / 10 percent Pd/C / ethanol / 15 h / 20 °C

6: 801 mg / potassium carbonate / tetrahydrofuran / 2 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; di-isopropyl azodicarboxylate; hydrogen; potassium carbonate; thiophenol; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Wittig-Still rearrangement / 2: Mitsunobu reaction;
DOI:10.1021/jo026803h

Reference yield:

: 517907-34-5
allyl-((1R,2S)-2-azidomethylcyclopent-3-enyl)-carbamic acid tert-butyl ester

: 517907-26-5
(2R,3'S)-1'-(3-phenylprop-2-ynoyl)-[2,3']bipiperidinyl-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: triphenylphosphine / tetrahydrofuran / 13 h / 60 °C

2: 176 mg / potassium carbonate / tetrahydrofuran / 3 h / 20 °C

3: 86 percent / NaH / dimethylformamide / 0.5 h / 0 - 20 °C

4: 80 percent / (IHMes)(Cy₃P)Cl₂Ru=CHPh / CH₂Cl₂ / 3 h / Heating

5: hydrogen / Pd/C / ethanol / 14 h / 20 °C

6: 801 mg / potassium carbonate / tetrahydrofuran / 2 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogen; sodium hydride; potassium carbonate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Staudinger reduction;
DOI:10.1021/jo026803h