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

Base Information

Chemical Name:(6S,7S,11S)-11-(benzyloxymethyl)-7-hydroxy-2-azaspiro[5.5]undec-8-en-1-one
CAS No.:1416815-15-0
Molecular Formula:C₁₈H₂₃NO₃
Molecular Weight:301.386
Hs Code.:

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

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

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

There total 4 articles about (6S,7S,11S)-11-(benzyloxymethyl)-7-hydroxy-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: 52.0%

: 1416815-14-9
(6R,11S)-11-(benzyloxymethyl)-2-azaspiro[5.5]undec-8-en-1-one

: 1416815-15-0
(6S,7S,11S)-11-(benzyloxymethyl)-7-hydroxy-2-azaspiro[5.5]undec-8-en-1-one

Guidance literature:: With selenium(IV) oxide; water; In ethanol; at 90 ℃; for 72h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ol3030764

Reference yield:

: 954148-38-0
methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

: 1416815-15-0
(6S,7S,11S)-11-(benzyloxymethyl)-7-hydroxy-2-azaspiro[5.5]undec-8-en-1-one

Guidance literature:: Multi-step reaction with 4 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

4.1: selenium(IV) oxide; water / ethanol / 72 h / 90 °C / Inert atmosphere

With selenium(IV) oxide; water; potassium hexamethylsilazane; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; water; toluene; 2.1: |Staudinger Azide Reduction;
DOI:10.1021/ol3030764

Reference yield:

: 1416815-29-6
methyl (1R,6S)-1-(3-azidopropyl)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate

: 1416815-15-0
(6S,7S,11S)-11-(benzyloxymethyl)-7-hydroxy-2-azaspiro[5.5]undec-8-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: selenium(IV) oxide; water / ethanol / 72 h / 90 °C / Inert atmosphere

With selenium(IV) oxide; water; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; water; 1: |Staudinger Azide Reduction;
DOI:10.1021/ol3030764