(4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one

Base Information

Chemical Name:(4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one
CAS No.:1114547-50-0
Molecular Formula:C₁₁H₁₀ClF₂NO₂
Molecular Weight:261.656
Hs Code.:

Synonyms:(4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one

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Chemical Property of (4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one

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Technology Process of (4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one

There total 6 articles about (4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one 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: 38.0%

: 1114547-48-6
(S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate

: 667-27-6
Ethyl bromodifluoroacetate

: 1114547-50-0
(4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one

: ethyl 2-{(4S,5R)-3-(3-chlorophenyl)-4-methyl-2-oxooxazolidin-5-yl}-2,2-difluoroacetate

Guidance literature:: (S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate; Ethyl bromodifluoroacetate; With zinc; In tetrahydrofuran; at 20 ℃; for 1h; Reflux; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

With diisopropylamine; In tetrahydrofuran; for 12h; Overall yield = 58 %; Overall yield = 16.2 g; Reflux; Inert atmosphere;
DOI:10.1016/j.bmc.2017.04.018

Reference yield: 21.0%

: 1114547-48-6
(S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate

: 667-27-6
Ethyl bromodifluoroacetate

: 1114547-50-0
(4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one

Guidance literature:: (S)-tert-butyl (3-chlorophenyl)(1-oxopropan-2-yl)carbamate; Ethyl bromodifluoroacetate; With zinc; In tetrahydrofuran; for 1h; Heating / reflux;

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 2h;

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 12h; Heating / reflux;

Reference yield:

: 625-99-0
3-iodochlorobenzene

: 1114547-50-0
(4S,5S)-1-(3-chlorophenyl)-3,3-difluoro-4-hydroxy-5-methylpyrrolidin-2-one

: ethyl 2-{(4S,5R)-3-(3-chlorophenyl)-4-methyl-2-oxooxazolidin-5-yl}-2,2-difluoroacetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium phosphate; copper(l) iodide / isopropyl alcohol; ethylene glycol / 24 h / 80 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 50 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

3.2: 6 h / -78 - 20 °C / Inert atmosphere

3.3: 20 h / 20 °C / Inert atmosphere

4.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.33 h / -65 - -55 °C / Inert atmosphere

4.2: 0.5 h / -65 - -55 °C / Inert atmosphere

5.1: zinc / tetrahydrofuran / 1 h / 20 °C / Reflux; Inert atmosphere

5.2: 2 h / 20 °C / Inert atmosphere

5.3: 12 h / Reflux; Inert atmosphere

With 1H-imidazole; potassium phosphate; copper(l) iodide; n-butyllithium; oxalyl dichloride; zinc; In tetrahydrofuran; hexane; dichloromethane; ethylene glycol; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; 1.1: |Ullmann-Goldberg Substitution / 4.1: |Swern Oxidation / 4.2: |Swern Oxidation;
DOI:10.1016/j.bmc.2017.04.018