benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate

Base Information

• Chemical Name: benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate
• CAS No.: 304436-18-8
• Molecular Formula: C₁₆H₂₀BrNO₃
• Molecular Weight: 354.244
• Mol file: 304436-18-8.mol

Synonyms:benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate

Chemical Property of benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate

There total 3 articles about benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-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: 87.0%

benzyl (2S,3S)-2-allyl-3-hydroxypiperidine-1-carboxylate (304436-17-7,244056-94-8) → benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate (304436-18-8,244056-98-2)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(00)01109-1

Reference yield:

Benzyl 2-allyl-3-oxo-1-piperidinecarboxylate (244056-97-1) → benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate (304436-18-8,244056-98-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / baker's yeast; sucrose; K₂CO₃ / H₂O; ethanol / 90 h / 15 °C

2: 87 percent / NBS / acetonitrile / 0.5 h / 20 °C

With N-Bromosuccinimide; baker's yeast; potassium carbonate; Sucrose; In ethanol; water; acetonitrile;

DOI:10.1016/S0040-4020(00)01109-1

Reference yield:

benzyl (R)-2-allyl-3-oxopiperidine-1-carboxylate (304436-21-3) → benzyl (3aS,7aS)-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate (304436-18-8,244056-98-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / K₂CO₃ / methanol / 4 h / 20 °C

2: 62 percent / baker's yeast; sucrose; K₂CO₃ / H₂O; ethanol / 90 h / 15 °C

3: 87 percent / NBS / acetonitrile / 0.5 h / 20 °C

With N-Bromosuccinimide; baker's yeast; potassium carbonate; Sucrose; In methanol; ethanol; water; acetonitrile;

DOI:10.1016/S0040-4020(00)01109-1

upstream raw materials:

benzyl (2S,3S)-2-allyl-3-hydroxypiperidine-1-carboxylate

Benzyl 2-allyl-3-oxo-1-piperidinecarboxylate

benzyl (R)-2-allyl-3-oxopiperidine-1-carboxylate

Downstream raw materials:

(+)-isofebrifugine

benzyl (3aS,7aS)-2-(bromomethyl)-2-methoxyhexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate

benzyl (3aS,7aS)-2-hydroxy-2-[(4-oxo-3(4H)-quinazolinyl)methyl]hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate