(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-3-carboxylic acid

Base Information

• Chemical Name: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-3-carboxylic acid
• CAS No.: 193693-68-4
• Molecular Formula: C21H21 N O4
• Molecular Weight: 351.402
• Hs Code.: 29333990
• European Community (EC) Number: 675-809-0
• DSSTox Substance ID: DTXSID00589229
• Nikkaji Number: J2.230.384H
• Wikidata: Q72500369
• Mol file: 193693-68-4.mol

Synonyms:193693-68-4;L-1-Fmoc-Nipecotic acid;(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-3-carboxylic acid;(s)-1-fmoc-piperidine-3-carboxylic acid;fmoc-(s)-nipecotic acid;(3S)-1-(9H-fluoren-9-ylmethoxycarbonyl)piperidine-3-carboxylic acid;(3S)-1-{[(9H-Fluoren-9-yl)methoxy]carbonyl}piperidine-3-carboxylic acid;1,3-PIPERIDINEDICARBOXYLIC ACID, 1-(9H-FLUOREN-9-YLMETHYL) ESTER, (3S)-;(3S)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]piperidine-3-carboxylic acid;FMOC-PIC(3)-OH;MFCD04112682;(s)-fmoc-nip;fmoc-(s)-nip;L-1-Fmoc-Nipecoticacid;SCHEMBL799721;DTXSID00589229;(s)-piperidine-1,3-dicarboxylic acid 1-(9h-fluoren-9-ylmethyl) ester;(s)-fmoc-piperidine-3-carboxylic acid;AKOS015837407;(3S)-1-Fmoc-3-piperidinecarboxylic acid;AS-10004;1-n-fmoc-piperidine-3(s)-carboxylic acid;CS-0131706;EN300-299520;A813662;Q-102977;(S)-1-Fmoc-piperidine-3-carboxylic acid, AldrichCPR;Z1436242321

Chemical Property of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.89E-13mmHg at 25°C
• Melting Point: 160-161℃
• Boiling Point: 561.6°Cat760mmHg
• PKA: 4.47±0.20(Predicted)
• Flash Point: 293.5°C
• PSA: 66.84000
• Density: 1.293g/cm³
• LogP: 3.67000
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 351.14705815
• Heavy Atom Count: 26
• Complexity: 514

Purity/Quality:

98%min ^*data from raw suppliers

Fmoc-L-nipecotic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CN(C1)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O
• Isomeric SMILES: C1C[C@@H](CN(C1)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O

Technology Process of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-3-carboxylic acid

There total 5 articles about (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-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:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-nipecotic acid (498-95-3,25137-00-2,59045-82-8,60252-41-7,262853-93-0) → (S)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}piperidine-3-carboxylic acid (193693-68-4) + (R)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}piperidine-3-carboxylic acid (193693-67-3)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 2h;

DOI:10.1002/hlca.200590157

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + nipecotic acid (498-95-3,262853-93-0) → (S)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}piperidine-3-carboxylic acid (193693-68-4)

Guidance literature:

nipecotic acid; With (+)-10-camphorsulfonic acid; In acetone; Heating;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1021/jo049103g

Reference yield:

5-bromovaleroyl chloride (4509-90-4) → (S)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}piperidine-3-carboxylic acid (193693-68-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: BuLi / tetrahydrofuran / 0.17 h / -30 °C

1.2: 87 percent / tetrahydrofuran / 2 h / 0 °C

2.1: TiCl₄; Et₃N / CH₂Cl₂ / 0.5 h / -15 °C

2.2: TiCl₄ / CH₂Cl₂ / 3 h / 0 °C

3.1: 80 percent / NaH; Bu₄NI / dimethylformamide / 3 h / 70 °C

4.1: 85 percent / H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 4 h / 0 °C

5.1: 148 mg / H₂ / Pd/C / methanol / 1.5 h

6.1: Na₂CO₃ / dioxane; H₂O / 2 h / 20 °C

With lithium hydroxide; n-butyllithium; hydrogen; dihydrogen peroxide; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Mannich reaction;

DOI:10.1002/hlca.200590157

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

nipecotic acid

(S)-nipecotic acid

5-bromovaleroyl chloride

Refernces

• 1、 Agarkov, Anton,Greenfield, Scott J.,Ohishi, Takahiro,Collibee, Scott E.,Gilbertson, Scott R.. "Catalysis with phosphine-containing amino acids in various "turn" motifs". . p. 8077 - 8085. Retrieved 2007/10/03.