(3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester

Base Information

• Chemical Name: (3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester
• CAS No.: 388108-48-3
• Molecular Formula: C₂₃H₃₄FN₃O₃
• Molecular Weight: 419.54
• Mol file: 388108-48-3.mol

Synonyms:(3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester

Chemical Property of (3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester

There total 7 articles about (3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl 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: 97.0%

(3R,4R)-4-benzyloxycarbonylamino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester (388108-46-1) → (3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester (388108-48-3)

Guidance literature:

In methanol; palladium;

Reference yield:

C31H42FN3O3 → (3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester (388108-48-3)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; at 20 ℃; under 3102.97 Torr;

DOI:10.1016/j.bmcl.2007.03.065

Reference yield:

1-tert-butyl 3-ethyl 4-oxopiperidine-1,3-dicarboxylate (98977-34-5) → (3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester (388108-48-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: p-TsOH / benzene / Heating

2.1: NaBH(OAc)3; HOAc / acetonitrile / 0 °C

2.2: K₂CO₃ / ethanol / Heating

3.1: tetrahydrofuran / 20 °C / Saponification

4.1: BOP; Et₃N / CH₂Cl₂ / 20 °C

5.1: H₂ / Pd(OH)2/C / ethanol / 20 °C / 3102.97 Torr

With hydrogen; sodium tris(acetoxy)borohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile; benzene;

DOI:10.1016/j.bmcl.2007.03.065

upstream raw materials:

1-tert-butyl 3-ethyl 4-oxopiperidine-1,3-dicarboxylate

(S)-3-(4-fluorobenzyl)-piperidine

(3R,4R)-1-(tert-butoxycarbonyl)-4-((R)-1-phenylethylamino)piperidine-3-carboxylic acid

4-((R)-1-phenylethylamino)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Downstream raw materials:

(3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester

(3R,4R)-4-[3-(5-acetyl-4-methyl-thiazol-2-yl)-ureido]-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester