(3R,5S)-3-Azido-1-((R)-2-hydroxy-1-phenyl-ethyl)-5-methylsulfanyl-piperidin-2-one

Base Information

Chemical Name:(3R,5S)-3-Azido-1-((R)-2-hydroxy-1-phenyl-ethyl)-5-methylsulfanyl-piperidin-2-one
CAS No.:178757-09-0
Molecular Formula:C₁₄H₁₈N₄O₂S
Molecular Weight:306.389
Hs Code.:

Synonyms:(3R,5S)-3-Azido-1-((R)-2-hydroxy-1-phenyl-ethyl)-5-methylsulfanyl-piperidin-2-one

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Chemical Property of (3R,5S)-3-Azido-1-((R)-2-hydroxy-1-phenyl-ethyl)-5-methylsulfanyl-piperidin-2-one

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Technology Process of (3R,5S)-3-Azido-1-((R)-2-hydroxy-1-phenyl-ethyl)-5-methylsulfanyl-piperidin-2-one

There total 4 articles about (3R,5S)-3-Azido-1-((R)-2-hydroxy-1-phenyl-ethyl)-5-methylsulfanyl-piperidin-2-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: 70.0%

: 178757-08-9
(3S,5S)-3-Bromo-1-((R)-2-hydroxy-1-phenyl-ethyl)-5-methylsulfanyl-piperidin-2-one

: 178757-09-0
(3R,5S)-3-Azido-1-((R)-2-hydroxy-1-phenyl-ethyl)-5-methylsulfanyl-piperidin-2-one

Guidance literature:: With sodium azide; acetic acid; In N,N-dimethyl-formamide; for 7h; Ambient temperature;
DOI:10.1016/S0040-4020(96)00340-7

Reference yield:

: 152555-04-9
Acetic acid (R)-2-(2,6-dioxo-piperidin-1-yl)-2-phenyl-ethyl ester

: 178757-09-0
(3R,5S)-3-Azido-1-((R)-2-hydroxy-1-phenyl-ethyl)-5-methylsulfanyl-piperidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LiBHEt₃, 2.) TFA / 1.) THF, -78 deg C, 2.5 h, 2.) CH₂CL₂, RT, 1.5 h

2: AIBN / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) RT, overnight

3: 1.) sec-BuLi, 2.) Br₂ / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 1 h 45 min

4: 70 percent / aq. NaN₃, AcOH / dimethylformamide / 7 h / Ambient temperature

With sodium azide; 2,2'-azobis(isobutyronitrile); bromine; sec.-butyllithium; lithium triethylborohydride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(96)00340-7

Reference yield:

: 178757-06-7
Acetic acid (R)-2-(2-oxo-3,4-dihydro-2H-pyridin-1-yl)-2-phenyl-ethyl ester

: 178757-09-0
(3R,5S)-3-Azido-1-((R)-2-hydroxy-1-phenyl-ethyl)-5-methylsulfanyl-piperidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: AIBN / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) RT, overnight

2: 1.) sec-BuLi, 2.) Br₂ / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 1 h 45 min

3: 70 percent / aq. NaN₃, AcOH / dimethylformamide / 7 h / Ambient temperature

With sodium azide; 2,2'-azobis(isobutyronitrile); bromine; sec.-butyllithium; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(96)00340-7