(3aR,6aR)-tert-butyl 1-((R)-1-phenylethyl)-6a-(pyridin-2-yl)tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate

Base Information

• Chemical Name: (3aR,6aR)-tert-butyl 1-((R)-1-phenylethyl)-6a-(pyridin-2-yl)tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate
• CAS No.: 1539317-16-2
• Molecular Formula: C₂₃H₂₉N₃O₃
• Molecular Weight: 395.502
• Mol file: 1539317-16-2.mol

Synonyms:(3aR,6aR)-tert-butyl 1-((R)-1-phenylethyl)-6a-(pyridin-2-yl)tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate

Chemical Property of (3aR,6aR)-tert-butyl 1-((R)-1-phenylethyl)-6a-(pyridin-2-yl)tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6aR)-tert-butyl 1-((R)-1-phenylethyl)-6a-(pyridin-2-yl)tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate

There total 1 articles about (3aR,6aR)-tert-butyl 1-((R)-1-phenylethyl)-6a-(pyridin-2-yl)tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-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:

tert-butyl N-allyl-N-[2-oxo-2-(2-pyridyl)ethyl]carbamate (1539317-15-1) + (R)-1-Phenylethylhydroxylamine (2912-98-3) → (3aR,6aR)-tert-butyl 1-((R)-1-phenylethyl)-6a-(pyridin-2-yl)tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate (1539317-16-2) + (3aS,6aS)-tert-butyl 1-((R)-1-phenylethyl)-6a-(pyridin-2-yl)tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate (1539317-24-2)

Guidance literature:

With titanium(IV) tetraethanolate; In tetrahydrofuran; at 70 - 80 ℃; for 97h; Overall yield = 3.143 g; Sealed tube;

Reference yield:

(3aR,6aR)-tert-butyl 1-((R)-1-phenylethyl)-6a-(pyridin-2-yl)tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate (1539317-16-2) → N-((4aR,7aR)-6-(5-fluoro-4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)-7a-(pyridin-2-yl)-4,4a.5,6.7.7a-hexahydropyrrolo[3,4-d][1,3]thiazin-2-yl)benzamide (1539317-22-0)

Guidance literature:

Multi-step reaction with 6 steps

1: palladium 10% on activated carbon; ammonium formate / methanol; water / 56 h / 65 °C

2: dichloromethane / 1.5 h / -15 °C

3: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 1 h / -40 °C

4: trifluoroacetic acid / dichloromethane / 4 h / 0 °C

5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 17 h / 20 °C

6: sodium ethanolate / ethanol / 2 h / Reflux

With pyridine; trifluoromethylsulfonic anhydride; palladium 10% on activated carbon; ammonium formate; sodium ethanolate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

(3aR,6aR)-tert-butyl 1-((R)-1-phenylethyl)-6a-(pyridin-2-yl)tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate (1539317-16-2) → N-((4aR,7aR)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-7a-(pyridin-2-yl)-4,4a.5,6.7.7a-hexahydropyrrolo[3,4-d][1,3]thiazin-2-yl)benzamide (1539317-23-1)

Guidance literature:

Multi-step reaction with 7 steps

1: palladium 10% on activated carbon; ammonium formate / methanol; water / 56 h / 65 °C

2: dichloromethane / 1.5 h / -15 °C

3: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 1 h / -40 °C

4: trifluoroacetic acid / dichloromethane / 4 h / 0 °C

5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 17 h / 20 °C

6: sodium ethanolate / ethanol / 2 h / Reflux

7: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C

With pyridine; trifluoromethylsulfonic anhydride; palladium 10% on activated carbon; ammonium formate; sodium ethanolate; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyl N-allyl-N-[2-oxo-2-(2-pyridyl)ethyl]carbamate

(R)-1-Phenylethylhydroxylamine

Downstream raw materials:

(3R,4R)-tert-butyl 3-(3-benzoylthioureido)-4-(hydroxymethyl)-3-(pyridin-2-yl)pyrrolidine-1-carboxylate

N-((4aR,7aR)-7a-(pyridin-2-yl)-4,4a.5,6.7.7a-hexahydropyrrolo[3,4-d][1,3]thiazin-2-yl)benzamide

N-((4aR,7aR)-6-carbamimidoyl-7a-(pyridin-2-yl)-4,4a.5,6.7.7a-hexahydropyrrolo[3,4-d][1,3]thiazin-2-yl)benzamide hydrochloride

N-((4aR,7aR)-6-(5-fluoro-4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)-7a-(pyridin-2-yl)-4,4a.5,6.7.7a-hexahydropyrrolo[3,4-d][1,3]thiazin-2-yl)benzamide