(+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate

Base Information

• Chemical Name: (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate
• CAS No.: 1427281-86-4
• Molecular Formula: C₃₀H₃₇NO₃
• Molecular Weight: 459.629
• Mol file: 1427281-86-4.mol

Synonyms:(+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate

Chemical Property of (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate

There total 3 articles about (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 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: 66.0%

danishefsky's diene (54125-02-9) + (S)-1-phenyl-ethylamine (2627-86-3) + (+)-(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl glyoxylate (849113-77-5) → (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate (1427281-86-4) + (1S,2S,5R)-8-phenylneomenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate (1431164-78-1)

Guidance literature:

(S)-1-phenyl-ethylamine; (+)-(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl glyoxylate; With zinc(II) iodide; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

danishefsky's diene; In tetrahydrofuran; at 20 ℃; for 72h; Overall yield = 79 %; Overall yield = 2.24 g; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2013.02.027

Reference yield:

(+)-(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate (849113-76-4) → (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate (1427281-86-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: osmium(VIII) oxide; sodium periodate

2.1: zinc(II) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Molecular sieve

2.2: 72 h / 20 °C / Inert atmosphere

With sodium periodate; osmium(VIII) oxide; zinc(II) iodide; In tetrahydrofuran; 2.2: |Diels-Alder Cycloaddition;

DOI:10.1016/j.tet.2013.02.027

Reference yield:

(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexan-1-ol (104870-75-9) → (+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate (1427281-86-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine; dmap

2.1: osmium(VIII) oxide; sodium periodate

3.1: zinc(II) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Molecular sieve

3.2: 72 h / 20 °C / Inert atmosphere

With dmap; sodium periodate; osmium(VIII) oxide; triethylamine; zinc(II) iodide; In tetrahydrofuran; 3.2: |Diels-Alder Cycloaddition;

DOI:10.1016/j.tet.2013.02.027

upstream raw materials:

danishefsky's diene

(S)-1-phenyl-ethylamine

(+)-(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl glyoxylate

(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexan-1-ol

Downstream raw materials:

(+)-(2R,4S)-2-(hydroxymethyl)-1-[(1S)-1-phenylethyl]piperidin-4-ol

(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexan-1-ol

(+)-(1S,2S,5R)-8-phenylneomenthyl (2R)-4-oxo-1-[(1S)-1-phenylethyl]piperidine-2-carboxylate