(3S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

Base Information

• Chemical Name: (3S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
• CAS No.: 145549-04-8
• Molecular Formula: C₁₉H₁₇NO₄
• Molecular Weight: 323.348
• Mol file: 145549-04-8.mol

Synonyms:(3S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

Chemical Property of (3S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

There total 5 articles about (3S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-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:

(3S,6S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-5-oxo-3-phenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester (1026734-17-7) → (3S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one (145549-04-8)

Guidance literature:

With ammonium formate; palladium on activated charcoal; Yield given. Multistep reaction; 1.) MeOH, 1.5 h, 2.) toluene, reflux, 1.5 h;

DOI:10.1021/jo00053a012

Reference yield:

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) → (3S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one (145549-04-8)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) ammonium formate / 1.) 5percent Pd/C / 1.) MeOH, 1.5 h, 2.) toluene, reflux, 1.5 h

With ammonium formate; palladium on activated charcoal;

DOI:10.1021/jo00053a012

Reference yield:

(3S,7aR)-5-oxo-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole (122383-34-0) → (3S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one (145549-04-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) lithium hexamethyldisilazane / 1.) THF, -78 deg C, 1 h, 2.) 15 min

2: 1.) phenylselenyl bromide, 2.) 30percent H₂O₂ / 1.) THF, 30 min, 2.) CH₂Cl₂, H₂O, a) 0 deg C, 30 min, b) 0 deg C to r.t., 30 min

4: 1.) ammonium formate / 1.) 5percent Pd/C / 1.) MeOH, 1.5 h, 2.) toluene, reflux, 1.5 h

With Phenylselenyl bromide; dihydrogen peroxide; ammonium formate; lithium hexamethyldisilazane; palladium on activated charcoal;

DOI:10.1021/jo00053a012

upstream raw materials:

(3S,6S,7R,7aR)-7-Benzo[1,3]dioxol-5-yl-5-oxo-3-phenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester

1,2-(methylenedioxy)-4-bromobenzene

(3S,7aR)-5-oxo-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole

(3S,7aR)-5-Oxo-3-phenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester

Downstream raw materials:

(S)-2-((R)-3-Benzo[1,3]dioxol-5-yl-pyrrolidin-1-yl)-2-phenyl-ethanol