Acetic acid (6R,7S)-2-benzyl-1-oxo-2-aza-spiro[5.5]undec-7-yl ester

Base Information

• Chemical Name: Acetic acid (6R,7S)-2-benzyl-1-oxo-2-aza-spiro[5.5]undec-7-yl ester
• CAS No.: 134746-07-9
• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 315.412
• Mol file: 134746-07-9.mol

Synonyms:Acetic acid (6R,7S)-2-benzyl-1-oxo-2-aza-spiro[5.5]undec-7-yl ester

Chemical Property of Acetic acid (6R,7S)-2-benzyl-1-oxo-2-aza-spiro[5.5]undec-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (6R,7S)-2-benzyl-1-oxo-2-aza-spiro[5.5]undec-7-yl ester

There total 5 articles about Acetic acid (6R,7S)-2-benzyl-1-oxo-2-aza-spiro[5.5]undec-7-yl 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:

N-benzyl-2-piperidinone (4783-65-7) → Acetic acid (6R,7S)-2-benzyl-1-oxo-2-aza-spiro[5.5]undec-7-yl ester (134746-07-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / LDA / tetrahydrofuran / 0.5 h / -78 - 25 °C

2: 1.) SeO₂, t-BuOOH; 2.) NaBH₄ / 1.) CH₂Cl₂, room temperature, 5 h; 2.) EtOH, - 20 deg C to room temperature, 30 min

3: 86 percent / CCl₄, PPh₃ / 5 h / Heating

4: 62 percent / KHMDS (0.005M) / tetrahydrofuran / -78 deg C, 1h; 55 deg C, 30 min.

5: 1.) OsO₄, NaIO₄; 2.) (CF₃CO)2O, 60percent H₂O₂, Na₂HPO₄ / 1.) acetone/H₂O, room temperature, 15 h; 2.) CH₂Cl₂, room temperature, 15 h

With tert.-butylhydroperoxide; tetrachloromethane; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; osmium(VIII) oxide; selenium(IV) oxide; dihydrogen peroxide; potassium hexamethylsilazane; triphenylphosphine; trifluoroacetic anhydride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)74276-6

Reference yield:

1-Benzyl-3-(6-methyl-hept-5-enyl)-piperidin-2-one (134746-03-5) → Acetic acid (6R,7S)-2-benzyl-1-oxo-2-aza-spiro[5.5]undec-7-yl ester (134746-07-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) SeO₂, t-BuOOH; 2.) NaBH₄ / 1.) CH₂Cl₂, room temperature, 5 h; 2.) EtOH, - 20 deg C to room temperature, 30 min

2: 86 percent / CCl₄, PPh₃ / 5 h / Heating

3: 62 percent / KHMDS (0.005M) / tetrahydrofuran / -78 deg C, 1h; 55 deg C, 30 min.

4: 1.) OsO₄, NaIO₄; 2.) (CF₃CO)2O, 60percent H₂O₂, Na₂HPO₄ / 1.) acetone/H₂O, room temperature, 15 h; 2.) CH₂Cl₂, room temperature, 15 h

With tert.-butylhydroperoxide; tetrachloromethane; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; osmium(VIII) oxide; selenium(IV) oxide; dihydrogen peroxide; potassium hexamethylsilazane; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)74276-6

Reference yield:

1-Benzyl-3-((E)-7-chloro-6-methyl-hept-5-enyl)-piperidin-2-one (134746-05-7) → Acetic acid (6R,7S)-2-benzyl-1-oxo-2-aza-spiro[5.5]undec-7-yl ester (134746-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / KHMDS (0.005M) / tetrahydrofuran / -78 deg C, 1h; 55 deg C, 30 min.

2: 1.) OsO₄, NaIO₄; 2.) (CF₃CO)2O, 60percent H₂O₂, Na₂HPO₄ / 1.) acetone/H₂O, room temperature, 15 h; 2.) CH₂Cl₂, room temperature, 15 h

With sodium periodate; disodium hydrogenphosphate; osmium(VIII) oxide; dihydrogen peroxide; potassium hexamethylsilazane; trifluoroacetic anhydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)74276-6

upstream raw materials:

(6R,7R)-2-Benzyl-7-isopropenyl-2-aza-spiro[5.5]undecan-1-one

N-benzyl-2-piperidinone

1-Benzyl-3-(6-methyl-hept-5-enyl)-piperidin-2-one

1-Benzyl-3-((E)-7-hydroxy-6-methyl-hept-5-enyl)-piperidin-2-one

Downstream raw materials:

(+/-)-N-benzyl isonitramine