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

Base Information

• Chemical Name: (2R,6R)-2-[2-(1,3-dioxan-2-yl)ethyl]-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methylpiperidine
• CAS No.: 503843-20-7
• Molecular Formula: C₂₀H₃₁NO₃
• Molecular Weight: 333.471
• Mol file: 503843-20-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (2R,6R)-2-[2-(1,3-dioxan-2-yl)ethyl]-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methylpiperidine 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%

(1,3-dioxan-2-yl)ethylmagnesium bromide + (3R,5R)-5-methyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (204845-25-0) → (2R,6R)-2-[2-(1,3-dioxan-2-yl)ethyl]-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methylpiperidine (503843-20-7)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 20h;

DOI:10.1021/jo0266083

Reference yield:

(3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine (152615-80-0) → (2R,6R)-2-[2-(1,3-dioxan-2-yl)ethyl]-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methylpiperidine (503843-20-7)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 71 percent / tetrahydrofuran / 20 h / 0 °C

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

DOI:10.1021/jo0266083

Reference yield:

(6R)-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methyl-2-piperidone (177981-20-3) → (2R,6R)-2-[2-(1,3-dioxan-2-yl)ethyl]-1-[(1R)-2-hydroxy-1-phenylethyl]-6-methylpiperidine (503843-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / Red-Al / tetrahydrofuran; toluene / 24 h / -78 °C

2: 71 percent / tetrahydrofuran / 20 h / 0 °C

With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene;

DOI:10.1021/jo0266083

upstream raw materials:

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

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

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

Downstream raw materials:

(5R,9R)-5-methylindolizidine