(2S,4R)-Fmoc-4-hydroxypiperidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4R)-Fmoc-4-hydroxypiperidine-2-carboxylic acid
• CAS No.: 917099-02-6
• Molecular Formula: C₂₁H₂₁NO₅
• Molecular Weight: 367.401
• Hs Code.: 29333990
• DSSTox Substance ID: DTXSID00373261
• Nikkaji Number: J1.999.592E
• Wikidata: Q82161413
• Mol file: 917099-02-6.mol

Synonyms:653589-37-8;(2S,4R)-FMOC-4-HYDROXYPIPERIDINE-2-CARBOXYLIC ACID;Fmoc-(2S,4R)-4-hydroxypiperidine-2-carboxylic acid;(2S,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-hydroxypiperidine-2-carboxylic acid;(2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-hydroxypiperidine-2-carboxylic acid;(2S,4R)-1-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-4-hydroxypiperidine-2-carboxylic acid;1,2-Piperidinedicarboxylic acid, 4-hydroxy-, 1-(9H-fluoren-9-ylmethyl)ester, (2S,4R)-;SCHEMBL800047;DTXSID00373261;MFCD04112684;AKOS025404041;AS-79358;E70679;EN300-6737130;EN300-7370271;(2S,4R)-FMOC-4-HYDROXYPIPERIDINE-2-CARBOXYLICACID;(2S,4R)-Fmoc-4-hydroxypiperidine-2-carboxylic acid, AldrichCPR;4alpha-Hydroxypiperidine-1,2alpha-dicarboxylic acid 1-(9H-fluorene-9-ylmethyl) ester;rac-(2R,4S)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-hydroxypiperidine-2-carboxylic acid

Chemical Property of (2S,4R)-Fmoc-4-hydroxypiperidine-2-carboxylic acid

Chemical Property:

• PSA: 87.07000
• LogP: 2.78330
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 367.14197277
• Heavy Atom Count: 27
• Complexity: 545

Purity/Quality:

97% ^*data from raw suppliers

(2R,4S)-Fmoc-4-hydroxypiperidine-2-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(C(CC1O)C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1CN([C@@H](C[C@@H]1O)C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of (2S,4R)-Fmoc-4-hydroxypiperidine-2-carboxylic acid

There total 10 articles about (2S,4R)-Fmoc-4-hydroxypiperidine-2-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:

1,2-di-tert-butyl (2S)-4,6-dioxopiperidine-1,2-dicarboxylate (653589-10-7) → (2S,4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-hydroxy-2-piperidinecarboxylic acid (917099-02-6)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₃CN; acetic acid / CH₂Cl₂ / 72 h / 20 °C

2: 100 percent / BH₃*SMe₂ / tetrahydrofuran / 20 °C

3: trifluroacetic acid / 2 h / 20 °C

4: 253 mg / potassium carbonate / H₂O; acetone / pH 9.0

With dimethylsulfide borane complex; sodium cyanoborohydride; potassium carbonate; acetic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1021/jo0353886

Reference yield:

1,2-di-tert-butyl (2S)-4,6-dioxopiperidine-1,2-dicarboxylate (653589-10-7) → (2S,4S)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-hydroxy-2-piperidinecarboxylic acid (917099-02-6)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₃CN; acetic acid / CH₂Cl₂ / 72 h / 20 °C

2: 100 percent / BH₃*SMe₂ / tetrahydrofuran / 20 °C

3: PPh₃; diisopropylazodicarboxylate / tetrahydrofuran / 0 - 20 °C

4: 211 mg / sodium hydroxide / dioxane; H₂O / 0.5 h / pH 9

5: trifluoroacetic acid / 2 h / 20 °C

6: 109 mg / potassium carbonate / H₂O; acetone

With sodium hydroxide; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; sodium cyanoborohydride; potassium carbonate; acetic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone; 3: Mitsunobu reaction;

DOI:10.1021/jo0353886

Reference yield:

di(tert-butyl) (2S,4R)-4-hydroxy-1,2-piperidinedicarboxylate (653589-35-6) → (2S,4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-hydroxy-2-piperidinecarboxylic acid (917099-02-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluroacetic acid / 2 h / 20 °C

2: 253 mg / potassium carbonate / H₂O; acetone / pH 9.0

With potassium carbonate; trifluoroacetic acid; In water; acetone;

DOI:10.1021/jo0353886

upstream raw materials:

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

(2S,4R)-4-hydroxypiperidine-2-carboxylic acid

1,2-di-tert-butyl (2S)-4,6-dioxopiperidine-1,2-dicarboxylate

di(tert-butyl) (2S,4R)-4-hydroxy-1,2-piperidinedicarboxylate

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