(2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentyl-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide

Base Information

Chemical Name:(2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentyl-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide
CAS No.:588940-74-3
Molecular Formula:C₂₅H₃₂ClNO₂S
Molecular Weight:446.054
Hs Code.:

Synonyms:(2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentyl-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide

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Chemical Property of (2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentyl-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide

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Technology Process of (2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentyl-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide

There total 6 articles about (2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentyl-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide 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: 67.0%

: 588940-69-6
(3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide

: 27935-87-1
cyclopentylmethyl Iodide

: 588940-74-3
(2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentyl-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide

Guidance literature:: (3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.833333h;

cyclopentylmethyl Iodide; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane; at -78 - 25 ℃; for 16.5h;

Reference yield: 67.0%

: 588940-69-6
(3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide

: 27935-87-1
cyclopentylmethyl Iodide

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 588940-74-3
(2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentyl-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide

Guidance literature:: With n-butyllithium; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ethyl acetate;

Reference yield:

: 393165-02-1
(3-chloro-4-methylsulfanyl-phenyl)-oxo-acetic acid methyl ester

: 588940-74-3
(2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentyl-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydroxide; water / toluene / 1.5 h / 50 - 60 °C / Inert atmosphere

2.1: hydrazine hydrate; potassium hydroxide / 16 h / -50 - 100 °C / Inert atmosphere

3.1: potassium carbonate; pivaloyl chloride / acetone / 0.33 h / -10 - 20 °C / Inert atmosphere

4.1: lithium hexamethyldisilazane; n-butyllithium / hexane; tetrahydrofuran / 0.83 h / -78 - 0 °C / Inert atmosphere

4.2: 16.5 h / -78 - 25 °C / Inert atmosphere

With n-butyllithium; water; pivaloyl chloride; potassium carbonate; hydrazine hydrate; potassium hydroxide; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; acetone; toluene;
DOI:10.1021/jm3008689