isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate

Base Information

• Chemical Name: isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate
• CAS No.: 369593-35-1
• Molecular Formula: C₁₇H₁₉NO₄
• Molecular Weight: 301.342
• Mol file: 369593-35-1.mol

Synonyms:isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate

Chemical Property of isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate

There total 2 articles about isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate 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:

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (103201-79-2,1820583-17-2) → isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate (369593-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C

1.2: tetrahydrofuran / 1.2 h / -78 - -20 °C

2.1: H₂O₂ / CH₂Cl₂ / 0.5 h / 0 °C

With dihydrogen peroxide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)01096-6

Reference yield:

isobutyl chloroformate (543-27-1) → isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate (369593-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C

1.2: tetrahydrofuran / 1.2 h / -78 - -20 °C

2.1: H₂O₂ / CH₂Cl₂ / 0.5 h / 0 °C

With dihydrogen peroxide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)01096-6

Reference yield: 97.0%

1-Bromo-4-fluorobenzene (460-00-4) + isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate (369593-35-1) → isobutyl (3S,6S,7R,7aR)-7-(4-fluorophenyl)-3-phenyl-5-oxo-tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate (369593-36-2)

Guidance literature:

1-Bromo-4-fluorobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With copper(l) iodide; In tetrahydrofuran; at -25 ℃; for 0.5h;

isobutyl (3S,7aR)-5-oxo-3-phenyl-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1002/1099-0690(200211)2002:21<3543::AID-EJOC3543>3.0.CO;2-0

upstream raw materials:

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

isobutyl chloroformate

Downstream raw materials:

isobutyl (3S,6S,7R,7aR)-7-(4-fluorophenyl)-3-phenyl-5-oxo-tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole-6-carboxylate

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

isobutyl (3S,4R)-1-benzyl-4-(4-fluorophenyl)piperidine-3-carboxylate

isobutyl (3S,4R,5S)-1-benzyl-5-chloro-4-(4-fluorophenyl)piperidine-3-carboxylate