(3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Base Information

• Chemical Name: (3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
• CAS No.: 204845-25-0
• Molecular Formula: C₁₄H₁₉NO
• Molecular Weight: 217.311
• Mol file: 204845-25-0.mol

Synonyms:(3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Chemical Property of (3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

There total 6 articles about (3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 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: 70.0%

(6R)-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methyl-2-piperidone (177981-20-3) → (3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (204845-25-0)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene; at -78 ℃; for 24h;

DOI:10.1021/jo0266083

Reference yield: 63.1%

(R)-2-[((R)-4-[1,3]Dioxolan-2-yl-1-methyl-butyl)-(2,4,6-trimethoxy-benzyl)-amino]-2-phenyl-ethanol (205526-51-8) → (3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (204845-25-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 72h; Ambient temperature;

DOI:10.3987/com-97-s32

Reference yield:

(3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine (152615-80-0) → (3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (204845-25-0)

Guidance literature:

Multi-step reaction with 2 steps

1: CuCN; BF₃*Et₂O / diethyl ether; tetrahydrofuran / 2 h / -78 °C

2: 70 percent / Red-Al / tetrahydrofuran; toluene / 24 h / -78 °C

With boron trifluoride diethyl etherate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1021/jo0266083

upstream raw materials:

(6R)-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methyl-2-piperidone

(R)-2-[((R)-4-[1,3]Dioxolan-2-yl-1-methyl-butyl)-(2,4,6-trimethoxy-benzyl)-amino]-2-phenyl-ethanol

(3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine

D-2-phenylglycinol

Downstream raw materials:

(2R)-1-[(1R)-2-hydroxy-1-phenylethyl]-2-methylpiperidine

(2R,6R)-2-[2-(1,3-dioxan-2-yl)ethyl]-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methylpiperidine

(+)-(2R)-2-methylpiperidine hydrochloride

(-)-pinidine