(2R,4'S)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione

Base Information

• Chemical Name: (2R,4'S)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione
• CAS No.: 1438394-48-9
• Molecular Formula: C₃₀H₂₇NO₂
• Molecular Weight: 433.55
• Mol file: 1438394-48-9.mol

Synonyms:

Chemical Property of (2R,4'S)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4'S)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione

There total 5 articles about (2R,4'S)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione 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:

E-styryl iodide (42599-24-6) + N-benzyl-1-oxo-N-(penta-3,4-dien-1-yl)indane-2-carboxamide (1438394-24-1) → (2R,4'S)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione (1438394-48-9) + (2S,4'R)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione

Guidance literature:

With silver orthophosphate; (4S,4'S)-2,2'-propane-2,2-diylbis{4-[(2S)-butan-2-yl]-4,5-dihydro-1,3-oxazole}; palladium diacetate; In 1,2-dichloro-ethane; at 70 ℃; for 36h; Overall yield = 61 %; Overall yield = 53 mg; stereoselective reaction; Sealed tube;

DOI:10.1039/c3cc42079e

Reference yield:

N-(tert-butoxycarbonyl)-N-benzyl-4-amino-1-butyne (142301-75-5) → (2R,4'S)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione (1438394-48-9) + (2S,4'R)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper(I) bromide; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 12 h / 100 °C

2.1: trifluoroacetic acid / dichloromethane

2.2: pH 8

3.1: toluene / Reflux

4.1: (4S,4'S)-2,2'-propane-2,2-diylbis{4-[(2S)-butan-2-yl]-4,5-dihydro-1,3-oxazole}; palladium diacetate; silver orthophosphate / 1,2-dichloro-ethane / 36 h / 70 °C / Sealed tube

With silver orthophosphate; (4S,4'S)-2,2'-propane-2,2-diylbis{4-[(2S)-butan-2-yl]-4,5-dihydro-1,3-oxazole}; palladium diacetate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; copper(I) bromide; In 1,4-dioxane; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1039/c3cc42079e

Reference yield:

C12H15N (1240792-17-9) → (2R,4'S)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione (1438394-48-9) + (2S,4'R)-1'-benzyl-4'-((E)-4-phenylbuta-1,3-dien-2-yl)spiro[indene-2,3'-piperidine]-1,2'(3H)-dione

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / Reflux

2: (4S,4'S)-2,2'-propane-2,2-diylbis{4-[(2S)-butan-2-yl]-4,5-dihydro-1,3-oxazole}; palladium diacetate; silver orthophosphate / 1,2-dichloro-ethane / 36 h / 70 °C / Sealed tube

With silver orthophosphate; (4S,4'S)-2,2'-propane-2,2-diylbis{4-[(2S)-butan-2-yl]-4,5-dihydro-1,3-oxazole}; palladium diacetate; In 1,2-dichloro-ethane; toluene;

DOI:10.1039/c3cc42079e

upstream raw materials:

E-styryl iodide

N-benzyl-1-oxo-N-(penta-3,4-dien-1-yl)indane-2-carboxamide

N-(tert-butoxycarbonyl)-N-benzyl-4-amino-1-butyne

C₁₂H₁₅N