(S)-2-Ethynyl-4-((R)-1-hydroxy-ethyl)-2H-quinoline-1-carboxylic acid phenyl ester

Base Information

• Chemical Name: (S)-2-Ethynyl-4-((R)-1-hydroxy-ethyl)-2H-quinoline-1-carboxylic acid phenyl ester
• CAS No.: 161824-80-2
• Molecular Formula: C₂₀H₁₇NO₃
• Molecular Weight: 319.36
• Mol file: 161824-80-2.mol

Synonyms:(S)-2-Ethynyl-4-((R)-1-hydroxy-ethyl)-2H-quinoline-1-carboxylic acid phenyl ester

Chemical Property of (S)-2-Ethynyl-4-((R)-1-hydroxy-ethyl)-2H-quinoline-1-carboxylic acid phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Ethynyl-4-((R)-1-hydroxy-ethyl)-2H-quinoline-1-carboxylic acid phenyl ester

There total 7 articles about (S)-2-Ethynyl-4-((R)-1-hydroxy-ethyl)-2H-quinoline-1-carboxylic acid phenyl 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:

(S)-4-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-ethynyl-2H-quinoline-1-carboxylic acid phenyl ester → (S)-2-Ethynyl-4-((R)-1-hydroxy-ethyl)-2H-quinoline-1-carboxylic acid phenyl ester (161824-80-2)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 11.5h; Yield given; Heating;

DOI:10.1016/0040-4020(95)00521-9

Reference yield:

phenyl chloroformate (1885-14-9) → (S)-2-Ethynyl-4-((R)-1-hydroxy-ethyl)-2H-quinoline-1-carboxylic acid phenyl ester (161824-80-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / CH₂Cl₂ / -78 °C

2: TBAF, MeOH / tetrahydrofuran / 0.42 h / 0 °C

3: TsOH*H₂O, MeOH / 11.5 h / Heating

With methanol; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(94)80032-4

Reference yield:

Acetic acid (R)-1-quinolin-4-yl-ethyl ester (161824-74-4) → (S)-2-Ethynyl-4-((R)-1-hydroxy-ethyl)-2H-quinoline-1-carboxylic acid phenyl ester (161824-80-2)

Guidance literature:

Multi-step reaction with 5 steps

2: 86 percent / imidazol / dimethylformamide / 19 h / 70 °C

3: 68 percent / CH₂Cl₂ / -78 °C

4: TBAF, MeOH / tetrahydrofuran / 0.42 h / 0 °C

5: TsOH*H₂O, MeOH / 11.5 h / Heating

With 1H-imidazole; methanol; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(94)80032-4

upstream raw materials:

phenyl chloroformate

Acetic acid (R)-1-quinolin-4-yl-ethyl ester

(R)-1-(4-quinolyl)ethanol

4-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-quinoline

Downstream raw materials:

(1aR,2R,7bS)-2-Ethynyl-7b-(1-hydroxy-1-methyl-ethyl)-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

(1aR,2R,7bS)-7b-Acetyl-2-ethynyl-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

(1aR,2R,7bS)-7b-Acetyl-2-((Z)-6-trimethylsilanyl-hex-3-ene-1,5-diynyl)-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

(1aR,2R,7bR)-2-Ethynyl-7b-((R)-1-hydroxy-ethyl)-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester