[(R)-3-((S)-Acetoxy-phenyl-methyl)-3-hydroxy-2-oxo-piperidin-1-yl]-acetic acid tert-butyl ester

Base Information

Chemical Name:[(R)-3-((S)-Acetoxy-phenyl-methyl)-3-hydroxy-2-oxo-piperidin-1-yl]-acetic acid tert-butyl ester
CAS No.:250248-81-8
Molecular Formula:C₂₀H₂₇NO₆
Molecular Weight:377.437
Hs Code.:

Synonyms:[(R)-3-((S)-Acetoxy-phenyl-methyl)-3-hydroxy-2-oxo-piperidin-1-yl]-acetic acid tert-butyl ester

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Chemical Property of [(R)-3-((S)-Acetoxy-phenyl-methyl)-3-hydroxy-2-oxo-piperidin-1-yl]-acetic acid tert-butyl ester

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Technology Process of [(R)-3-((S)-Acetoxy-phenyl-methyl)-3-hydroxy-2-oxo-piperidin-1-yl]-acetic acid tert-butyl ester

There total 7 articles about [(R)-3-((S)-Acetoxy-phenyl-methyl)-3-hydroxy-2-oxo-piperidin-1-yl]-acetic acid tert-butyl ester 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: 77.0%

: 108-24-7
acetic anhydride

: 250248-79-4
[(R)-3-Hydroxy-3-((S)-hydroxy-phenyl-methyl)-2-oxo-piperidin-1-yl]-acetic acid tert-butyl ester

: 250248-81-8
[(R)-3-((S)-Acetoxy-phenyl-methyl)-3-hydroxy-2-oxo-piperidin-1-yl]-acetic acid tert-butyl ester

Guidance literature:: With pyridine; dmap; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1016/S0960-894X(99)00448-5

Reference yield:

: 675-20-7
piperidin-2-one

: 250248-81-8
[(R)-3-((S)-Acetoxy-phenyl-methyl)-3-hydroxy-2-oxo-piperidin-1-yl]-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

2: 33 percent / NaH; AcOH / methanol; tetrahydrofuran / 5 - 20 °C

3: 100 percent / lithium bis-trimethylsilylamide / tetrahydrofuran / 0 - 20 °C

4: 46 percent / 2 percent K₂OsO₄; AD-mix alpha; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 20 °C

5: 77 percent / pyridine; DMAP / tetrahydrofuran / 0 - 20 °C

With pyridine; dmap; potassium osmate(VI); AD-mix-α; methanesulfonamide; sodium hydride; acetic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 1: protection / 2: Condensation / 3: Alkylation / 4: dihydroxylation / 5: Acetylation;
DOI:10.1016/S0960-894X(99)00448-5

Reference yield:

: 3326-13-4
N-acetyl-2-piperidone

: 250248-81-8
[(R)-3-((S)-Acetoxy-phenyl-methyl)-3-hydroxy-2-oxo-piperidin-1-yl]-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 56 percent / NaH; AcOH / methanol; tetrahydrofuran / 5 - 20 °C

2: 100 percent / lithium bis-trimethylsilylamide / tetrahydrofuran / 0 - 20 °C

3: 46 percent / 2 percent K₂OsO₄; AD-mix alpha; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 20 °C

4: 77 percent / pyridine; DMAP / tetrahydrofuran / 0 - 20 °C

With pyridine; dmap; potassium osmate(VI); AD-mix-α; methanesulfonamide; sodium hydride; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water; tert-butyl alcohol; 1: Condensation / 2: Alkylation / 3: dihydroxylation / 4: Acetylation;
DOI:10.1016/S0960-894X(99)00448-5