(+/-)-lycoramine

Base Information

• Chemical Name: (+/-)-lycoramine
• CAS No.: 18797-70-1
• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.375
• Mol file: 18797-70-1.mol

Synonyms:(+/-)-lycoramine

Chemical Property of (+/-)-lycoramine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (+/-)-lycoramine

There total 1 articles about (+/-)-lycoramine 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:

5-bromo-2-methoxyphenol (37942-01-1) → (+/-)-lycoramine (18797-70-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 8.5 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / 16 h / 0 - 20 °C / Inert atmosphere

2.2: -78 - 0 °C / Inert atmosphere

3.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 4 h / 20 °C / Inert atmosphere

4.1: hydrogenchloride / methanol; acetone; water / 45 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere

6.2: 1.33 h / -60 - 20 °C / Inert atmosphere

7.1: di(rhodium)tetracarbonyl dichloride; tris(pentafluorophenyl)phosphine / tetrahydrofuran / 19 h / 130 °C / Inert atmosphere; Glovebox; Sealed tube

8.1: sodium acetate; hydroxylamine hydrochloride / methanol / 1.5 h / 20 °C / Inert atmosphere

9.1: p-toluenesulfonyl chloride; dmap; triethylamine / dichloromethane / 1.33 h / 0 - 20 °C / Inert atmosphere

9.2: 30 °C / Inert atmosphere

10.1: sodium hydride / tetrahydrofuran / 4.33 h / 0 - 20 °C / Inert atmosphere

10.2: 5 h / 30 °C / Inert atmosphere

11.1: L-Selectride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

11.2: 1.67 h / -78 - 70 °C / Inert atmosphere

With hydrogenchloride; dmap; n-butyllithium; di(rhodium)tetracarbonyl dichloride; hydroxylamine hydrochloride; sodium acetate; L-Selectride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; tris(pentafluorophenyl)phosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 3.1: |Dess-Martin Oxidation / 6.1: |Wittig Olefination / 6.2: |Wittig Olefination / 9.1: |Beckmann Rearrangement / 9.2: |Beckmann Rearrangement;

DOI:10.1021/acs.orglett.9b04337

upstream raw materials:

5-bromo-2-methoxyphenol