(S)-6-(5-amino-2-fluorophenyl)-6-methyl-5-azaspiro[2.5]octane-4-thione

Base Information

Chemical Name:(S)-6-(5-amino-2-fluorophenyl)-6-methyl-5-azaspiro[2.5]octane-4-thione
CAS No.:1446318-52-0
Molecular Formula:C₁₄H₁₇FN₂S
Molecular Weight:264.367
Hs Code.:

Synonyms:(S)-6-(5-amino-2-fluorophenyl)-6-methyl-5-azaspiro[2.5]octane-4-thione

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Chemical Property of (S)-6-(5-amino-2-fluorophenyl)-6-methyl-5-azaspiro[2.5]octane-4-thione

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Technology Process of (S)-6-(5-amino-2-fluorophenyl)-6-methyl-5-azaspiro[2.5]octane-4-thione

There total 14 articles about (S)-6-(5-amino-2-fluorophenyl)-6-methyl-5-azaspiro[2.5]octane-4-thione 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:

: 1446318-51-9
C₂₇H₂₅FN₂S

: 1446318-52-0
(S)-6-(5-amino-2-fluorophenyl)-6-methyl-5-azaspiro[2.5]octane-4-thione

Guidance literature:: With hydrogenchloride; In 1,4-dioxane; water; at 23 ℃; for 1h;
DOI:10.1016/j.bmcl.2013.05.003

Reference yield:

: (R)-N-((1E)-1-(5-bromo-2-fluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide

: 1446318-52-0
(S)-6-(5-amino-2-fluorophenyl)-6-methyl-5-azaspiro[2.5]octane-4-thione

Guidance literature:: Multi-step reaction with 13 steps

1: zinc; indium(III) triflate / tetrahydrofuran / 44 h / 18 - 23 °C / Inert atmosphere

2: hydrogenchloride / methanol; 1,4-dioxane / 1.5 h / 0 - 23 °C

3: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 23 °C

4: triethylamine / dichloromethane / 1 h / 0 °C

5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 96 h / 100 °C / Inert atmosphere

6: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 60 h / 23 °C / Inert atmosphere

7: lithium borohydride / tetrahydrofuran / 16 h / 23 °C / Cooling

8: triphenylphosphine; tetrachloromethane / dichloromethane / 16 h / 23 °C

9: lithium hexamethyldisilazane / tetrahydrofuran / 4 h / -10 - 23 °C

10: trifluoroacetic acid / 16 h / 23 °C

11: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium t-butanolate; tert-butyl XPhos / toluene / 16 h / 105 °C / Inert atmosphere; Sealed tube

12: Lawessons reagent / 1,4-dioxane / 3 h / 80 °C

13: hydrogenchloride / 1,4-dioxane; water / 1 h / 23 °C

With indium(III) triflate; Lawessons reagent; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; tetrachloromethane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium borohydride; 5%-palladium/activated carbon; hydrogen; sodium tris(acetoxy)borohydride; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; sodium t-butanolate; zinc; tert-butyl XPhos; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; toluene; 11: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.bmcl.2013.05.003

Reference yield:

: 198477-89-3
1-(5-bromo-2-fluorophenyl)ethan-1-one

: 1446318-52-0
(S)-6-(5-amino-2-fluorophenyl)-6-methyl-5-azaspiro[2.5]octane-4-thione

Guidance literature:: Multi-step reaction with 14 steps

1: titanium(IV) tetraethanolate / tetrahydrofuran / 18 h / 75 °C

2: zinc; indium(III) triflate / tetrahydrofuran / 44 h / 18 - 23 °C / Inert atmosphere

3: hydrogenchloride / methanol; 1,4-dioxane / 1.5 h / 0 - 23 °C

4: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 23 °C

5: triethylamine / dichloromethane / 1 h / 0 °C

6: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 96 h / 100 °C / Inert atmosphere

7: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 60 h / 23 °C / Inert atmosphere

8: lithium borohydride / tetrahydrofuran / 16 h / 23 °C / Cooling

9: triphenylphosphine; tetrachloromethane / dichloromethane / 16 h / 23 °C

10: lithium hexamethyldisilazane / tetrahydrofuran / 4 h / -10 - 23 °C

11: trifluoroacetic acid / 16 h / 23 °C

12: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium t-butanolate; tert-butyl XPhos / toluene / 16 h / 105 °C / Inert atmosphere; Sealed tube

13: Lawessons reagent / 1,4-dioxane / 3 h / 80 °C

14: hydrogenchloride / 1,4-dioxane; water / 1 h / 23 °C

With indium(III) triflate; Lawessons reagent; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; tetrachloromethane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; titanium(IV) tetraethanolate; lithium borohydride; 5%-palladium/activated carbon; hydrogen; sodium tris(acetoxy)borohydride; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; sodium t-butanolate; zinc; tert-butyl XPhos; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; toluene; 12: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.bmcl.2013.05.003