(2S,3R)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate

Base Information

• Chemical Name: (2S,3R)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate
• CAS No.: 1378532-38-7
• Molecular Formula: C₃₃H₃₃F₆NO₆
• Molecular Weight: 653.619
• Mol file: 1378532-38-7.mol

Synonyms:(2S,3R)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate

Chemical Property of (2S,3R)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate

There total 8 articles about (2S,3R)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate 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: 94.0%

(+)-(2S,3R)-3-hydroxy-1-(phenylmethyl)piperidine-2-methanol (105888-81-1) + (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) → (2S,3R)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate (1378532-38-7)

Guidance literature:

(+)-(2S,3R)-3-hydroxy-1-(phenylmethyl)piperidine-2-methanol; (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

With silica gel; In diethyl ether; hexane;

DOI:10.1002/hlca.201100507

Reference yield:

1-benzyl-2-(hydroxymethyl)piperidin-3-ol → (2S,3R)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate (1378532-38-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / -20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -60 °C

3.1: sodium tetrahydroborate / ethanol / -15 °C

3.2: -15 - 20 °C

4.1: Chiralcel_.(R). OD / hexane; iso-butanol

5.1: water; potassium hydroxide / ethanol / 3 h / 20 °C

6.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; water; dimethyl sulfoxide; triethylamine; potassium hydroxide; In ethanol; hexane; dichloromethane; iso-butanol;

DOI:10.1002/hlca.201100507

Reference yield:

rac-(1-benzyl-3-oxopiperidin-2-yl)methyl 2,2-dimethylpropanoate (817196-16-0) → (2S,3R)-1-(phenylmethyl)-2-{[(2R)-3,3,3-trifluoro-2-methoxy-1-oxo-2-phenylpropoxy]methyl}piperidin-3-yl (αR)-α-methoxy-α-(trifluoromethyl)benzeneacetate (1378532-38-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate / ethanol / -15 °C

1.2: -15 - 20 °C

2.1: Chiralcel_.(R). OD / hexane; iso-butanol

3.1: water; potassium hydroxide / ethanol / 3 h / 20 °C

4.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; water; triethylamine; potassium hydroxide; In ethanol; hexane; dichloromethane; iso-butanol;

DOI:10.1002/hlca.201100507

upstream raw materials:

3-hydroxy-2-hydroxymethylpyridine

(+)-(2S,3R)-[3-(acetyloxy)-1-(phenylmethyl)piperidin-2-yl]methyl 2,2-dimethylpropanoate

(+)-(2S,3R)-3-hydroxy-1-(phenylmethyl)piperidine-2-methanol

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride