(R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoic acid

Base Information

Chemical Name:(R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoic acid
CAS No.:1563182-91-1
Molecular Formula:C₂₄H₂₅Cl₂FN₂O₄
Molecular Weight:495.378
Hs Code.:

Synonyms:(R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoic acid

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Chemical Property of (R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoic acid

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Technology Process of (R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoic acid

There total 7 articles about (R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoic acid 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: 43.0%

: 1036926-64-3
6-fluoro-1-methylspiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one

: 1563182-90-0
(R)-3-(3,4-dichlorophenyl)-5-hydroxy-3-methyldihydrofuran-2(3H)-one

: 1563182-91-1
(R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoic acid

Guidance literature:: 6-fluoro-1-methylspiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one; (R)-3-(3,4-dichlorophenyl)-5-hydroxy-3-methyldihydrofuran-2(3H)-one; In dichloromethane; at 20 ℃; for 18h; Molecular sieve; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1021/ml400528y

Reference yield:

: 79099-07-3
N-tert-butyloxycarbonylpiperidin-4-one

: 1563182-91-1
(R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 4.5 h / -78 - -15 °C / Inert atmosphere

1.2: 0.42 h / -78 °C / Inert atmosphere

1.3: 13 h / -78 - 70 °C / Inert atmosphere

2.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere; Molecular sieve

3.1: trifluoroacetic acid / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

4.1: dichloromethane / 18 h / 20 °C / Molecular sieve; Inert atmosphere

4.2: 24 h / 20 °C / Inert atmosphere

With tert.-butyl lithium; caesium carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ml400528y

Reference yield:

: 173457-29-9
2-(3,4-dichloro-phenyl)-pent-4-enoic acid methyl ester

: 1563182-91-1
(R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 5 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: lithium hydroxide; water / methanol / 10 h / Reflux

3.1: ethyl acetate / Resolution of racemate; Inert atmosphere

4.1: hydrogenchloride / ethyl acetate; water

5.1: osmium(VIII) oxide; sodium periodate / tetrahydrofuran; water / 18 h / 20 °C / Darkness

6.1: dichloromethane / 18 h / 20 °C / Molecular sieve; Inert atmosphere

6.2: 24 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; water; sodium hydride; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ml400528y