(1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(S)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane

Base Information

Chemical Name:(1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(S)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane
CAS No.:1394910-44-1
Molecular Formula:C₂₁H₂₅NOS
Molecular Weight:339.502
Hs Code.:

Synonyms:(1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(S)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane

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Chemical Property of (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(S)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane

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Technology Process of (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(S)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane

There total 6 articles about (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(S)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane 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: 60.0%

: 1394910-32-7
(1S,4S,5R)-2-[(S)-1-phenylethyl]-4-phenylsulfanyl-2-azabicyclo[3.2.1]octane

: 1394910-44-1
(1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(S)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane

: (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(R)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane

Guidance literature:: With bis(acetylacetonate)oxovanadium; (S)-(-)-N-(3-phenyl-5-nitrosalicylidene)valinol; dihydrogen peroxide; In dichloromethane; at 0 ℃; for 20h; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.tet.2012.07.028

Reference yield:

: 2627-86-3
(S)-1-phenyl-ethylamine

: 1394910-44-1
(1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(S)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane

: (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(R)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 5 steps

2: palladium on activated charcoal; hydrogen; potassium carbonate

3: lithium aluminium tetrahydride

4: tributylphosphine / toluene / 72 h / 80 °C / Inert atmosphere

5: bis(acetylacetonate)oxovanadium; (S)-(-)-N-(3-phenyl-5-nitrosalicylidene)valinol; dihydrogen peroxide / dichloromethane / 20 h / 0 °C

With lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; tributylphosphine; (S)-(-)-N-(3-phenyl-5-nitrosalicylidene)valinol; palladium on activated charcoal; hydrogen; dihydrogen peroxide; potassium carbonate; In dichloromethane; toluene; 1: Diels-Alder reaction;
DOI:10.1016/j.tet.2012.07.028

Reference yield:

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 1394910-44-1
(1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(S)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane

: (1S,4S,5R)-2-[(S)-1-phenylethyl]-4-[(R)-phenylsulfinyl]-2-azabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 5 steps

2: palladium on activated charcoal; hydrogen; potassium carbonate

3: lithium aluminium tetrahydride

4: tributylphosphine / toluene / 72 h / 80 °C / Inert atmosphere

5: bis(acetylacetonate)oxovanadium; (S)-(-)-N-(3-phenyl-5-nitrosalicylidene)valinol; dihydrogen peroxide / dichloromethane / 20 h / 0 °C

With lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; tributylphosphine; (S)-(-)-N-(3-phenyl-5-nitrosalicylidene)valinol; palladium on activated charcoal; hydrogen; dihydrogen peroxide; potassium carbonate; In dichloromethane; toluene; 1: Diels-Alder reaction;
DOI:10.1016/j.tet.2012.07.028