1-[(3,4-dihydro-1(2H)-quinolinyl)carbonyl]-4-piperidinecarboxylic acid

Base Information

• Chemical Name: 1-[(3,4-dihydro-1(2H)-quinolinyl)carbonyl]-4-piperidinecarboxylic acid
• CAS No.: 100021-19-0
• Molecular Formula: C₁₆H₂₃NO₄
• Molecular Weight: 293.363
• Mol file: 100021-19-0.mol

Synonyms:1-[(3,4-dihydro-1(2H)-quinolinyl)carbonyl]-4-piperidinecarboxylic acid

Chemical Property of 1-[(3,4-dihydro-1(2H)-quinolinyl)carbonyl]-4-piperidinecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-[(3,4-dihydro-1(2H)-quinolinyl)carbonyl]-4-piperidinecarboxylic acid

There total 5 articles about 1-[(3,4-dihydro-1(2H)-quinolinyl)carbonyl]-4-piperidinecarboxylic 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: 88.0%

(+/-)-(1α,2β,3α,4α,5β)-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol (100021-16-7) → (+/-)-(1β,2α,3β,4α,5α)-4,5-(dimethylmethylenedioxy)-2-hydroxy-3-<(phenylmethoxy)methyl>-1-cyclopentanamine (100021-19-0)

Guidance literature:

With hydrogen; Lindlar's catalyst; In methanol; for 12h; under 760 Torr;

DOI:10.1021/jo00358a023

Reference yield:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → (+/-)-(1β,2α,3β,4α,5α)-4,5-(dimethylmethylenedioxy)-2-hydroxy-3-<(phenylmethoxy)methyl>-1-cyclopentanamine (100021-19-0)

Guidance literature:

Multi-step reaction with 5 steps

1: O₂, thiourea, sodium acetate, Rose bengal / methanol / 9 h / -5 °C / Irradiation

2: 62 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 48 h / Ambient temperature

3: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C

4: 92 percent / 75percent aq. HClO₄ / acetone / 1 h / Ambient temperature

5: 88 percent / H₂ / Lindlar catalyst / methanol / 12 h / 760 Torr

With sodium azide; perchloric acid; hydrogen; oxygen; sodium acetate; rose bengal; thiourea; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00358a023

Reference yield:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) → (+/-)-(1β,2α,3β,4α,5α)-4,5-(dimethylmethylenedioxy)-2-hydroxy-3-<(phenylmethoxy)methyl>-1-cyclopentanamine (100021-19-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 48 h / Ambient temperature

2: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C

3: 92 percent / 75percent aq. HClO₄ / acetone / 1 h / Ambient temperature

4: 88 percent / H₂ / Lindlar catalyst / methanol / 12 h / 760 Torr

With sodium azide; perchloric acid; hydrogen; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00358a023

upstream raw materials:

(+/-)-(1α,2β,3α,4α,5β)-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol

5-(benzyloxymethyl)cyclopentadiene

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane

Downstream raw materials:

(+/-)-(1α,2β,3α,4α,5β)-2-<(5-amino-6-chloro-4-pyrimidinyl)amino>-5-<(phenylmethoxy)methyl>-3,4-(dimethylmethylenedioxy)-1-cyclopentanol

(+/-)-(1β,2α,3β,4α,5α)-1-(6-amino-9H-purin-9-yl)-4,5-(dimethylmethylenedioxy)-2-<(1-imidazolylthiocarbonyl)oxy>-3-<(phenylmethoxy)methyl>cyclopentane

(+/-)-(1α,2β,3α,4α,5β)-2-(6-amino-9H-purin-9-yl)-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol

(+/-)-(1α,2β,3α,4α,5β)-2-(6-chloro-9H-purin-9-yl)-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol