(3R,4S)-4-Methoxycarbonylmethyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3R,4S)-4-Methoxycarbonylmethyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 132846-05-0
• Molecular Formula: C₂₄H₂₈N₂O₆Se
• Molecular Weight: 519.456
• Mol file: 132846-05-0.mol

Synonyms:

Chemical Property of (3R,4S)-4-Methoxycarbonylmethyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-4-Methoxycarbonylmethyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester

There total 8 articles about (3R,4S)-4-Methoxycarbonylmethyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-piperidine-1-carboxylic acid benzyl 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:

(4aR,8aR)-1,2,3,4,4a,5,8,8a-Octahydro-isoquinoline (4492-15-3,25886-59-3,90607-81-1,132883-50-2) → (3R,4S)-4-Methoxycarbonylmethyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester (132846-05-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 2 N aq. NaOH / tetrahydrofuran / 10 h

2: KMnO₄, Aliquat^R 336 / CH₂Cl₂; H₂O / 3 h / 0 - 25 °C

3: CH₂Cl₂; diethyl ether / 0 °C

4: 93 percent / 0.1 M aq. NaOH / dimethylsulfoxide / 25 °C / phosphate buffer pH 7.0-7.2, pig liver esterase (PLE)

5: 86 percent / borane-methyl sulfide complex / tetrahydrofuran / 18 h / -78 °C

6: 82 percent / tributylphosphine / tetrahydrofuran; pyridine / 0.75 h / Ambient temperature

With sodium hydroxide; potassium permanganate; tributylphosphine; dimethylsulfide borane complex; Aliquat 336; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0957-4166(00)80445-0

Reference yield:

(1R,2R)-1-methanol-2-acetonitrile-4-cyclohexene (132883-48-8) → (3R,4S)-4-Methoxycarbonylmethyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester (132846-05-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / pyridine / CH₂Cl₂ / 0 - 25 °C

2: LiAlH₄, AlCl₃ / diethyl ether; tetrahydrofuran / 3 h / Ambient temperature

3: 2 N aq. NaOH / tetrahydrofuran / 10 h

4: KMnO₄, Aliquat^R 336 / CH₂Cl₂; H₂O / 3 h / 0 - 25 °C

5: CH₂Cl₂; diethyl ether / 0 °C

6: 93 percent / 0.1 M aq. NaOH / dimethylsulfoxide / 25 °C / phosphate buffer pH 7.0-7.2, pig liver esterase (PLE)

7: 86 percent / borane-methyl sulfide complex / tetrahydrofuran / 18 h / -78 °C

8: 82 percent / tributylphosphine / tetrahydrofuran; pyridine / 0.75 h / Ambient temperature

With pyridine; sodium hydroxide; potassium permanganate; lithium aluminium tetrahydride; aluminium trichloride; tributylphosphine; dimethylsulfide borane complex; Aliquat 336; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0957-4166(00)80445-0

Reference yield:

(1R,2R)-1-methanol-2-acetonitrile-4-cyclohexene acetate (132883-47-7) → (3R,4S)-4-Methoxycarbonylmethyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester (132846-05-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / KOH / methanol; H₂O / 2 h

2: 94 percent / pyridine / CH₂Cl₂ / 0 - 25 °C

3: LiAlH₄, AlCl₃ / diethyl ether; tetrahydrofuran / 3 h / Ambient temperature

4: 2 N aq. NaOH / tetrahydrofuran / 10 h

5: KMnO₄, Aliquat^R 336 / CH₂Cl₂; H₂O / 3 h / 0 - 25 °C

6: CH₂Cl₂; diethyl ether / 0 °C

7: 93 percent / 0.1 M aq. NaOH / dimethylsulfoxide / 25 °C / phosphate buffer pH 7.0-7.2, pig liver esterase (PLE)

8: 86 percent / borane-methyl sulfide complex / tetrahydrofuran / 18 h / -78 °C

9: 82 percent / tributylphosphine / tetrahydrofuran; pyridine / 0.75 h / Ambient temperature

With pyridine; potassium hydroxide; sodium hydroxide; potassium permanganate; lithium aluminium tetrahydride; aluminium trichloride; tributylphosphine; dimethylsulfide borane complex; Aliquat 336; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0957-4166(00)80445-0

upstream raw materials:

(4aR,8aR)-1,2,3,4,4a,5,8,8a-Octahydro-isoquinoline

(1R,2R)-1-methanol-2-acetonitrile-4-cyclohexene

(1R,2R)-1-methanol-2-acetonitrile-4-cyclohexene acetate

(1R,2R)-1-methanol-2-acetonitrile-4-cyclohexene mesylate