1-CBZ-2-PROPYL-PIPERIDIN-4-ONE

Base Information

• Chemical Name: 1-CBZ-2-PROPYL-PIPERIDIN-4-ONE
• CAS No.: 142764-70-3
• Molecular Formula: C16H21NO3
• Molecular Weight: 275.348
• Hs Code.: 2933399090
• Mol file: 142764-70-3.mol

Synonyms:1-Cbz-2-propylpiperidin-4-one;

Chemical Property of 1-CBZ-2-PROPYL-PIPERIDIN-4-ONE

Chemical Property:

• PSA: 46.61000
• LogP: 3.09470

Purity/Quality:

98%min ^*data from raw suppliers

Benzyl4-oxo-2-propylpiperidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-CBZ-2-PROPYL-PIPERIDIN-4-ONE

There total 11 articles about 1-CBZ-2-PROPYL-PIPERIDIN-4-ONE 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: 90.0%

n-propylmagnesium bromide (927-77-5) + benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate (185847-84-1) → N-(benzyloxycarbonyl)-(6S)-6-n-propylpiperidin-4-one (142764-70-3)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; In dichloromethane; at -78 ℃; for 12h; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201906237

Reference yield: 81.0%

N-(benzyloxycarbonyl)-(6S)-2,3-didehydro-6-n-propylpiperidin-4-one (142764-69-0) → N-(benzyloxycarbonyl)-(6S)-6-n-propylpiperidin-4-one (142764-70-3)

Guidance literature:

With L-Selectride; In tetrahydrofuran;

Reference yield:

N-<(S)-1-carboxy-(S)-2-methylbutyl>-(6S)-2,3-didehydro-6-n-propylpiperidin-4-one (142764-67-8) → N-(benzyloxycarbonyl)-(6S)-6-n-propylpiperidin-4-one (142764-70-3)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N, diphenyl phosphorazidate / toluene / 1.) room temperature, 2.) 40 deg C, 72 h

2: H₂ / 5percent Pd/C / methanol / 5 h / 760 Torr / Ambient temperature

3: 1.) BuLi / 1.) THF, hexane, 2.) warmed to room temperature, 50 min

4: 81 percent / L-Selectride / 1.) -78 deg C, 15 min, 2.) -78 deg C to room temperature, 30 min

With n-butyllithium; diphenyl phosphoryl azide; hydrogen; L-Selectride; triethylamine; palladium on activated charcoal; In methanol; toluene;

DOI:10.1021/jo00042a027

upstream raw materials:

N-(benzyloxycarbonyl)-(6S)-2,3-didehydro-6-n-propylpiperidin-4-one

(6S)-2,3-didehydro-6-n-propylpiperidin-4-one

benzyl chloroformate

N-<(S)-1-carboxy-(S)-2-methylbutyl>-(6S)-2,3-didehydro-6-n-propylpiperidin-4-one

Downstream raw materials:

(S)-coniine hydrochloride

benzyl (S)-2-propylpiperidine-1-carboxylate

N-(benzyloxycarbonyl)-(6S)-4-(1,3-dithiolan-4-yl)-6-n-propylpiperidine

Refernces

• 1、 Waldmann, H.,Braun, M.. "Asymmetric Tandem Mannich-Michael Reactions of Amino Acid Ester Imines with Danishefsky's Diene". . p. 4444 - 4451. Retrieved 2007/10/02.