(6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one

Base Information

• Chemical Name: (6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one
• CAS No.: 1416815-14-9
• Molecular Formula: C₁₈H₂₃NO₂
• Molecular Weight: 285.386
• Mol file: 1416815-14-9.mol

Synonyms:(6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one

Chemical Property of (6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one

There total 3 articles about (6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one 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:

methyl (1R,6S)-1-(3-aminopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate (1416815-30-9) → (6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one (1416815-14-9)

Guidance literature:

With potassium carbonate; In methanol; water; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol3030764

Reference yield:

methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate (954148-38-0) → (6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one (1416815-14-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 2 h / -78 °C / Inert atmosphere

1.2: 18 h / -78 - 20 °C / Inert atmosphere

2.1: triphenylphosphine; water / tetrahydrofuran / 2 h / Reflux; Inert atmosphere

3.1: potassium carbonate / methanol; water / 18 h / 20 °C / Inert atmosphere

With water; potassium hexamethylsilazane; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; water; toluene; 2.1: |Staudinger Azide Reduction;

DOI:10.1021/ol3030764

Reference yield:

methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate (1416815-29-6) → (6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one (1416815-14-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; water / tetrahydrofuran / 2 h / Reflux; Inert atmosphere

2: potassium carbonate / methanol; water / 18 h / 20 °C / Inert atmosphere

With water; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; water; 1: |Staudinger Azide Reduction;

DOI:10.1021/ol3030764

upstream raw materials:

methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

methyl (1R,6S)-1-(3-aminopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

Downstream raw materials:

(6S,7S,11S)-11-(benzyloxymethyl)-7-hydroxy-2-azaspiro[5.5]undec-8-en-1-one

(6S,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-ene-1,7-dione

C₁₈H₂₃NO₃

(6S,7R,11S)-11-(benzyloxymethyl)-7-(triisopropylsilyloxy)-2-azaspiro[5.5]undec-8-en-1-one