1-[(Benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acid

Base Information

• Chemical Name: 1-[(Benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acid
• CAS No.: 174543-78-3
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.32
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID90692938
• Mol file: 174543-78-3.mol

Synonyms:174543-78-3;1-N-CBZ-3-METHYLPIPERIDINE-3-CARBOXYLIC ACID;1-[(benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acid;1-Cbz-3-methylpiperidine-3-carboxylic Acid;3-methyl-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid;1-Cbz-3-methyl-3-piperidinecarboxylic acid;MFCD11559118;SCHEMBL1468742;3-Methyl-piperidine-1,3-dicarboxylic acid 1-benzyl ester;DTXSID90692938;AMY34566;AKOS012434886;AC-6328;SB11972;DS-13416;SY018682;CS-0052708;FT-0713349;1-N-Cbz-3-methyl-piperidine-3-carboxylicacid;A26681;EN300-121350;1-N-CBZ-3-METHYLPIPERIDINE-3-CARBOXYLICACID;1-(benzyloxycarbonyl)-3-methylpiperidine-3-carboxylic acid;3-Methyl-1,3-piperidinedicarboxylic acid 1-(phenylmethyl) ester

Chemical Property of 1-[(Benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acid

Chemical Property:

• Refractive Index: 1.555
• Boiling Point: 440.3 °C at 760 mmHg
• PKA: 4.52±0.20(Predicted)
• Flash Point: 220.1 °C
• PSA: 66.84000
• Density: 1.224 g/cm³
• LogP: 2.44780
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 277.13140809
• Heavy Atom Count: 20
• Complexity: 365

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-N-Cbz-3-Methylpiperidine-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCN(C1)C(=O)OCC2=CC=CC=C2)C(=O)O

Technology Process of 1-[(Benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acid

There total 8 articles about 1-[(Benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acid 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: 92.0%

1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate (664364-60-7) → 1-((benzyloxy)carbonyl)-3-methylpiperidine-3-carboxylic acid (174543-78-3)

Guidance literature:

1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate; With water; lithium hydroxide; In ethanol; at 86 ℃; for 1h;

With potassium hydrogensulfate; In water; pH=3 - 4;

Reference yield: 78.0%

3-Methyl-piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester (174543-82-9) → 1-((benzyloxy)carbonyl)-3-methylpiperidine-3-carboxylic acid (174543-78-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water;

DOI:10.1016/0040-4039(95)02378-X

Reference yield:

N-benzyloxycarbonyl nipecotic acid methyl ester (174543-74-9) → 1-((benzyloxy)carbonyl)-3-methylpiperidine-3-carboxylic acid (174543-78-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / LiN(TMS)2, DMPU / tetrahydrofuran / -60 °C / to room temperature

2: 78 percent / NaOH / tetrahydrofuran; H₂O

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; water;

DOI:10.1016/0040-4039(95)02378-X

upstream raw materials:

3-Methyl-piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

1-benzyloxycarbonylpiperidine-3-carboxylic acid

benzyl chloroformate

N-benzyloxycarbonyl nipecotic acid methyl ester

Downstream raw materials:

3-Carbamoyl-3-methyl-piperidine-1-carboxylic acid benzyl ester

tert-butyl N-(3-methyl-3-piperidinyl)carbamate

rac-benzyl 3-((tert-butoxycarbonyl)amino)-3-methylpiperidine-1-carboxylate

3-Acetylamino-3-methyl-piperidine-1-carboxylic acid benzyl ester

Refernces

• 1、 -. "Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme". Page/Page column 41. . Retrieved 2008/06/13.