(2S,4R)-1-benzyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S,4R)-1-benzyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate
• CAS No.: 133192-45-7
• Molecular Formula: C₁₅H₁₉NO₅
• Molecular Weight: 293.32
• Hs Code.: 2933399990
• European Community (EC) Number: 696-383-2
• Nikkaji Number: J1.614.953E
• Mol file: 133192-45-7.mol

Synonyms:133192-45-7;CIS-4-HYDROXY-PIPERIDINE-1,2-DICARBOXYLIC ACID 1-BENZYL ESTER 2-METHYL ESTER;cis-4-hydroxy-piperidine- 1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester;403503-37-7;(2S,4R)-1-benzyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate;1-O-benzyl 2-O-methyl (2S,4R)-4-hydroxypiperidine-1,2-dicarboxylate;Cis-1-benzyl2-methyl4-hydroxypiperidine-1,2-dicarboxylate;1-BENZYL 2-METHYL (2S,4R)-4-HYDROXYPIPERIDINE-1,2-DICARBOXYLATE;UZYUNWAMEQIRQH-OLZOCXBDSA-N;Cis-1-benzyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate;SCHEMBL1694132;Cbz-(2s, 4r)-4-hydroxy-piperidine-2-carboxylic acid methyl ester;AM803159;CS-0444736;EN300-20775362;EN300-20813351;rac-1-benzyl 2-methyl (2R,4S)-4-hydroxypiperidine-1,2-dicarboxylate;cis-4-hydroxypiperidine- 1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester;1,2-Piperidinedicarboxylic acid, 4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2S,4R)-rel-

Chemical Property of (2S,4R)-1-benzyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 99-100 °C
• Boiling Point: 436.1±45.0 °C(Predicted)
• PKA: 14.38±0.40(Predicted)
• Density: 1.272±0.06 g/cm3(Predicted)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 293.12632271
• Heavy Atom Count: 21
• Complexity: 367

Purity/Quality:

98%min ^*data from raw suppliers

Cis-1-benzyl2-methyl4-hydroxypiperidine-1,2-dicarboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1CC(CCN1C(=O)OCC2=CC=CC=C2)O
• Isomeric SMILES: COC(=O)[C@@H]1C[C@@H](CCN1C(=O)OCC2=CC=CC=C2)O

Technology Process of (2S,4R)-1-benzyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate

There total 2 articles about (2S,4R)-1-benzyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate 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%

methyl cis-4-hydroxy-2-piperidinecarboxylate (133192-44-6,189952-45-2) + benzyl chloroformate (501-53-1,94274-21-2) → 2-methyl 1-(phenylmethyl) cis-4-hydroxy-1,2-piperidinedicarboxylate (133192-45-7,1357348-22-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1002/jhet.5570430539

Reference yield:

(1α,5α)-2-(phenylmethyl)-6-oxa-2-azabicyclo<3.2.1>octan-7-one (133192-43-5) → 2-methyl 1-(phenylmethyl) cis-4-hydroxy-1,2-piperidinedicarboxylate (133192-45-7,1357348-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / 20percent Pd/C / 2.2 h / 2606.4 Torr

2: 84 percent / Et₃N / CH₂Cl₂ / 1 h / 5 °C

With hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane;

DOI:10.1021/jo00012a061

Reference yield: 95.0%

2-methyl 1-(phenylmethyl) cis-4-hydroxy-1,2-piperidinedicarboxylate (133192-45-7,1357348-22-1) + methanesulfonyl chloride (124-63-0) → 2-methyl cis-1-benzyloxycarbonyl-4-[(methylsulfonyl)oxy]piperidine-2-carboxylate

Guidance literature:

With pyridine; dmap; at 20 ℃; for 14h;

DOI:10.1002/jhet.5570430539

upstream raw materials:

methyl cis-4-hydroxy-2-piperidinecarboxylate

benzyl chloroformate

(1α,5α)-2-(phenylmethyl)-6-oxa-2-azabicyclo<3.2.1>octan-7-one

Downstream raw materials:

(2S,4R)-4-Hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester

2-methyl trans-1-benzyloxycarbonyl-4-aminopiperidine-2-carboxylate

2-methyl cis-1-benzyloxycarbonyl-4-aminopiperidine-2-carboxylate

bis(phenylmethyl) cis-4-hydroxy-1,2-piperidinedicarboxylate