(3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Base Information

• Chemical Name: (3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester
• CAS No.: 388108-32-5
• Molecular Formula: C₂₁H₃₂N₂O₄
• Molecular Weight: 376.496
• Mol file: 388108-32-5.mol

Synonyms:(3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Chemical Property of (3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

There total 6 articles about (3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl 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: 41.0%

1-(tert-butyl) 3-ethyl (3S,4R)-4-(((R)-1-phenylethyl)amino)piperidine-1,3-dicarboxylate (388109-78-2) → (3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (388108-32-5)

Guidance literature:

With sodium ethanolate; In ethanol; at 50 ℃; for 3h;

Reference yield:

4-((R)-1-phenylethylamino)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (532977-39-2) → 1-(tert-butyl) 3-ethyl (3S,4R)-4-(((R)-1-phenylethyl)amino)piperidine-1,3-dicarboxylate (388109-78-2) + (3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (388108-32-5)

Guidance literature:

4-((R)-1-phenylethylamino)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester; With sodium tris(acetoxy)borohydride; acetic acid; In acetonitrile; at 0 ℃;

With potassium carbonate; In ethanol; Further stages.; Heating;

DOI:10.1016/j.bmcl.2007.03.065

Reference yield:

(R)-1-phenyl-ethyl-amine (3886-69-9) → (3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (388108-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: p-TsOH / benzene / Heating

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

2.2: K₂CO₃ / ethanol / Heating

With sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; acetic acid; In acetonitrile; benzene;

DOI:10.1016/j.bmcl.2007.03.065

upstream raw materials:

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

(R)-1-phenyl-ethyl-amine

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

1-(tert-butyl) 3-ethyl (3S,4R)-4-(((R)-1-phenylethyl)amino)piperidine-1,3-dicarboxylate

Downstream raw materials:

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

(3R,4R)-4-aminopiperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl 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

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