(3R,4S)-3-Carboxymethyl-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3R,4S)-3-Carboxymethyl-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 132846-03-8
• Molecular Formula: C₁₈H₂₃NO₆
• Molecular Weight: 349.384
• Mol file: 132846-03-8.mol

Synonyms:(3R,4S)-3-Carboxymethyl-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid benzyl ester

Chemical Property of (3R,4S)-3-Carboxymethyl-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-3-Carboxymethyl-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid benzyl ester

There total 7 articles about (3R,4S)-3-Carboxymethyl-4-methoxycarbonylmethyl-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: 93.0%

(3R,4S)-1-benzyloxycarbonyl-3,4-piperidine diacetic acid dimethyl ester (132846-02-7) → (3R,4S)-3-Carboxymethyl-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid benzyl ester (132846-03-8)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; at 25 ℃; phosphate buffer pH 7.0-7.2, pig liver esterase (PLE);

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

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)-3-Carboxymethyl-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid benzyl ester (132846-03-8)

Guidance literature:

Multi-step reaction with 4 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)

With sodium hydroxide; potassium permanganate; Aliquat 336; In tetrahydrofuran; 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)-3-Carboxymethyl-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid benzyl ester (132846-03-8)

Guidance literature:

Multi-step reaction with 6 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)

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

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

upstream raw materials:

(3R,4S)-1-benzyloxycarbonyl-3,4-piperidine diacetic acid dimethyl ester

(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

Downstream raw materials:

(3R,4S)-3-(2-Hydroxy-ethyl)-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid benzyl ester

N-benzyloxycarbonyl meroquinene methyl ester

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