3-((3S,5S,8aS)-3-Phenyl-8a-trifluoromethyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-propan-1-ol

Base Information

• Chemical Name: 3-((3S,5S,8aS)-3-Phenyl-8a-trifluoromethyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-propan-1-ol
• CAS No.: 220453-22-5
• Molecular Formula: C₁₇H₂₂F₃NO₂
• Molecular Weight: 329.362
• Mol file: 220453-22-5.mol

Synonyms:3-((3S,5S,8aS)-3-Phenyl-8a-trifluoromethyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-propan-1-ol

Chemical Property of 3-((3S,5S,8aS)-3-Phenyl-8a-trifluoromethyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((3S,5S,8aS)-3-Phenyl-8a-trifluoromethyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-propan-1-ol

There total 5 articles about 3-((3S,5S,8aS)-3-Phenyl-8a-trifluoromethyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-propan-1-ol 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: 83.0%

3-(3-phenyl-8a-trifluoromethyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridin-5-yl)-prop-2-yn-1-ol (220453-14-5) → 3-((3S,5S,8aS)-3-Phenyl-8a-trifluoromethyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-propan-1-ol (220453-22-5)

Guidance literature:

With hydrogen; platinum(IV) oxide; In toluene; under 2327.17 Torr;

DOI:10.1021/ja983389n

Reference yield:

trifluoro-methanesulfonic acid 3-phenyl-8a-trifluoromethyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridin-5-yl ester (220453-09-8) → 3-((3S,5S,8aS)-3-Phenyl-8a-trifluoromethyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-propan-1-ol (220453-22-5)

Guidance literature:

Multi-step reaction with 2 steps

1: PdCl₂(PPh₃)2; CuI; i-Pr₂NH / tetrahydrofuran / 12 h / 20 °C

2: H₂ / PtO₂ / toluene / 18 h / 2585.74 Torr

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; hydrogen; diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; toluene;

DOI:10.1016/j.bmcl.2003.12.101

Reference yield:

(2S)-2-phenylglycinol (20989-17-7) → 3-((3S,5S,8aS)-3-Phenyl-8a-trifluoromethyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-propan-1-ol (220453-22-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / p-toluenesulfonic acid

2: 1.) KHMDS / 1.) -78 deg C

3: 76 percent / CuI

4: 83 percent / H₂ / PtO₂ / toluene / 2327.17 Torr

With copper(l) iodide; hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; platinum(IV) oxide; In toluene;

DOI:10.1021/ja983389n

upstream raw materials:

3-(3-phenyl-8a-trifluoromethyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridin-5-yl)-prop-2-yn-1-ol

trifluoro-methanesulfonic acid 3-phenyl-8a-trifluoromethyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridin-5-yl ester

(2S)-2-phenylglycinol

6,6,6-trifluoro-5-oxohexanoic acid

Downstream raw materials:

(3S,5S,8aS)-5-Allyl-3-phenyl-8a-trifluoromethyl-hexahydro-oxazolo[3,2-a]pyridine