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

Base Information

• Chemical Name: (3R,4R)-1-(tert-butoxycarbonyl)-4-((R)-1-phenylethylamino)piperidine-3-carboxylic acid
• CAS No.: 532977-52-9
• Molecular Formula: C₁₉H₂₈N₂O₄
• Molecular Weight: 348.442
• Mol file: 532977-52-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (3R,4R)-1-(tert-butoxycarbonyl)-4-((R)-1-phenylethylamino)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: 71.0%

(3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (388108-32-5) → (3R,4R)-1-(tert-butoxycarbonyl)-4-((R)-1-phenylethylamino)piperidine-3-carboxylic acid (532977-52-9)

Guidance literature:

(3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester; With sodium ethanolate; In ethanol; at 20 - 50 ℃; for 51h;

With hydrogenchloride; In ethanol; water; pH=4 - 5;

Reference yield:

(3R,4R)-4-((R)-1-Phenyl-ethylamino)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester; hydrochloride → (3R,4R)-1-(tert-butoxycarbonyl)-4-((R)-1-phenylethylamino)piperidine-3-carboxylic acid (532977-52-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; ethanol; water; at 0 ℃; for 16h;

DOI:10.1002/ejoc.200390112

Reference yield:

ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride (1454-53-1) → (3R,4R)-1-(tert-butoxycarbonyl)-4-((R)-1-phenylethylamino)piperidine-3-carboxylic acid (532977-52-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / HCO₂NH₄ / Pd/C / ethanol / 1 h / Heating

2.1: NaHCO₃; NaCl / CHCl₃; H₂O / 15 h / Heating

3.1: 13.7 g / p-TsOH / benzene / 7 h / Heating

4.1: 95 percent / NaBH₄; isobutyric acid / toluene / 7 h / 0 °C

5.1: sodium / ethanol / 15 h / 50 °C

5.2: 2.07 g / HCl / diethyl ether; dioxane / 1 h

6.1: LiOH*H₂O / tetrahydrofuran; ethanol; H₂O / 16 h / 0 °C

With lithium hydroxide; sodium tetrahydroborate; ammonium formate; sodium; sodium hydrogencarbonate; toluene-4-sulfonic acid; isobutyric Acid; sodium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; chloroform; water; toluene; benzene;

DOI:10.1002/ejoc.200390112

upstream raw materials:

(3R,4R)-4-((R)-1-phenylethylamino)piperidine-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

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)-piperidine-1-carbonyl]-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

(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

4-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester