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

Base Information

• Chemical Name: (3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate
• CAS No.: 244056-98-2
• Molecular Formula: C₁₆H₂₀BrNO₃
• Molecular Weight: 354.244
• DSSTox Substance ID: DTXSID70441249
• Nikkaji Number: J1.196.764G
• Mol file: 244056-98-2.mol

Synonyms:244056-98-2;(3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate;benzyl (3aS,7aS)-2-(bromomethyl)-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyridine-4-carboxylate;-4(2H)-carboxylate;-4(2H)-carboxylate";DTXSID70441249;GKBRQWNILJEDKY-FGRDXJNISA-N;AKOS025294980;(3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-b]pyridine;(3abeta,7abeta)-2-(Bromomethyl)octahydrofuro[3,2-b]pyridine-4-carboxylic acid benzyl ester

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.567
• Boiling Point: 460.038°C at 760 mmHg
• PKA: -1.35±0.40(Predicted)
• Flash Point: 232.023°C
• PSA: 38.77000
• Density: 1.387g/cm³
• LogP: 3.27790
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 353.06266
• Heavy Atom Count: 21
• Complexity: 359

Purity/Quality:

97% ^*data from raw suppliers

(3aS*,7aS*)-Benzyl2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(CC(O2)CBr)N(C1)C(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1C[C@H]2[C@H](CC(O2)CBr)N(C1)C(=O)OCC3=CC=CC=C3

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

There total 12 articles about (3aS*,7aS*)-Benzyl 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: 86.0%

(2S*,3S*)-Benzyl 2-allyl-3-hydroxy-1-piperidinecarboxylate (244056-94-8) → (3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate (244056-98-2)

Guidance literature:

With N-Bromosuccinimide; at 20 ℃;

DOI:10.2174/1570178616666190417115639

Reference yield:

1-Benzyl-3-hydroxypyridinium chloride (3323-73-7) → (3aS*,7aS*)-Benzyl 2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate (244056-98-2)

Guidance literature:

Multi-step reaction with 6 steps

1: NaH / methanol / Heating

2: NaBH₄ / methanol / 0 °C

3: tetrahydrofuran / 20 °C

4: BF₃*OEt₂ / acetonitrile / 20 °C

5: NaBH₄ / methanol / 0 °C

6: NBS / acetonitrile / 20 °C

With sodium tetrahydroborate; N-Bromosuccinimide; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; methanol; acetonitrile; 4: Claisen rearrangement;

DOI:10.1021/jm0302086

upstream raw materials:

(2S*,3S*)-Benzyl 2-allyl-3-hydroxy-1-piperidinecarboxylate

3-HYDROXYPYRIDINE

1-Benzyl-3-hydroxypyridinium chloride

5-(Allyloxy)-1-benzyl-1,2,3,6-tetrahydropyridine

Downstream raw materials:

(+)-isofebrifugine

febrifugine

dl-febrifugine

5-methyl-2,3-dihydro-1H-pyrrolizine