N-Boc-norloline

Base Information

• Chemical Name: N-Boc-norloline
• CAS No.: 1315552-07-8
• Molecular Formula: C₁₂H₂₀N₂O₃
• Molecular Weight: 240.302
• Mol file: 1315552-07-8.mol

Synonyms:

Chemical Property of N-Boc-norloline

Chemical Property:

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

N-[(2R,3R,3aS,4S,6aS)-hexahydro-2,4-methano-4H-furo[3,2-b]pyrrol-3-yl]carbamicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-[(2R,3R,3aS,4S,6aS)-hexahydro-2,4-methano-4H-furo[3,2-b]pyrrol-3-yl]carbamic Acid 1,1-Dimethylethyl Ester is an intermediate in the synthesis of Loline (I707255), an alkaloid isolated from fungal endophytes, an endosymbiont that lives within a plant.

Technology Process of N-Boc-norloline

There total 16 articles about N-Boc-norloline 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: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + C7H10N4O (1315552-06-7) → N-Boc-norloline (1315552-07-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1038/nchem.1072

Reference yield: 72.0%

benzyl (2S,3R,3aS,6aS)-3-((tert-butoxycarbonyl)amino)-2-(((methylsulfonyl)oxy)methyl)hexahydro-4H-furo[3,2-b]pyrrole-4-carboxylate → N-Boc-norloline (1315552-07-8)

Guidance literature:

With palladium hydroxide, 20 wt% on carbon; hydrogen; In methanol; for 1.5h; Inert atmosphere;

DOI:10.1021/jo502493e

Reference yield:

C15H17NO5S → N-Boc-norloline (1315552-07-8)

Guidance literature:

Multi-step reaction with 5 steps

1: lithium azide; water / N,N-dimethyl-formamide / 2.5 h / 130 °C / Inert atmosphere

2: bromine / 0 h / 12 °C / Inert atmosphere; Darkness

3: lithium chloride / N,N-dimethyl-formamide / 6 h / 105 °C / Inert atmosphere

4: potassium carbonate / methanol / 0.17 h / 150 °C / Inert atmosphere; Microwave irradiation

5: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere

With lithium azide; palladium 10% on activated carbon; water; hydrogen; bromine; potassium carbonate; lithium chloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1038/nchem.1072

upstream raw materials:

C₇H₁₁ClN₄O

di-tert-butyl dicarbonate

C₇H₁₀N₄O

Downstream raw materials:

(+)-Loline

N-formylloline

(+)-Loline dihydrochloride