(R)-2-(3,4-dichlorophenyl)-2-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanoic acid

Base Information

• Chemical Name: (R)-2-(3,4-dichlorophenyl)-2-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanoic acid
• CAS No.: 1563182-97-7
• Molecular Formula: C₂₄H₂₆Cl₂N₂O₃
• Molecular Weight: 461.388

Synonyms:(R)-2-(3,4-dichlorophenyl)-2-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanoic acid

Chemical Property of (R)-2-(3,4-dichlorophenyl)-2-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (R)-2-(3,4-dichlorophenyl)-2-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanoic acid

There total 6 articles about (R)-2-(3,4-dichlorophenyl)-2-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanoic 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: 60.0%

(R)-3-(3,4-dichlorophenyl)-5-hydroxy-3-methyldihydrofuran-2(3H)-one (1563182-90-0) + 1-methylspiro<3H-indole-3,4'-piperidin>-2(1H)-one (67677-81-0) → (R)-2-(3,4-dichlorophenyl)-2-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanoic acid (1563182-97-7)

Guidance literature:

(R)-3-(3,4-dichlorophenyl)-5-hydroxy-3-methyldihydrofuran-2(3H)-one; 1-methylspiro<3H-indole-3,4'-piperidin>-2(1H)-one; In 1,2-dichloro-ethane; 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:

3,4-dichlorophenyl acetic acid (5807-30-7) → (R)-2-(3,4-dichlorophenyl)-2-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanoic acid (1563182-97-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; pentane / 2 h / -25 °C / Inert atmosphere

1.2: 1.27 h / -25 - 20 °C / Inert atmosphere

2.1: thionyl chloride / 11.33 h / 20 °C / Inert atmosphere; Cooling with ice

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

3.2: 2 h / 20 °C / Inert atmosphere

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

5.1: ethyl acetate / Resolution of racemate; Inert atmosphere

6.1: hydrogenchloride / ethyl acetate; water

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

8.1: 1,2-dichloro-ethane / 18 h / 20 °C / Molecular sieve; Inert atmosphere

8.2: 24 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; water; sodium hydride; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil; pentane;

DOI:10.1021/ml400528y

Reference yield:

2-(S)-(3,4-dichloro-phenyl)-4-pentenoic acid (79333-48-5) → (R)-2-(3,4-dichlorophenyl)-2-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanoic acid (1563182-97-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: thionyl chloride / 11.33 h / 20 °C / Inert atmosphere; Cooling with ice

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

2.2: 2 h / 20 °C / Inert atmosphere

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

4.1: ethyl acetate / Resolution of racemate; Inert atmosphere

5.1: hydrogenchloride / ethyl acetate; water

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

7.1: 1,2-dichloro-ethane / 18 h / 20 °C / Molecular sieve; Inert atmosphere

7.2: 24 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; water; sodium hydride; lithium hydroxide; In tetrahydrofuran; methanol; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ml400528y

upstream raw materials:

3,4-dichlorophenyl acetic acid

2-(S)-(3,4-dichloro-phenyl)-4-pentenoic acid

2-(3,4-dichloro-phenyl)-pent-4-enoic acid methyl ester

(R)-3-(3,4-dichlorophenyl)-5-hydroxy-3-methyldihydrofuran-2(3H)-one

Downstream raw materials:

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-2-methyl-4-(1-methyl-2-oxospiro[indoline-3,4'-piperidine]-1'-yl)butanamido)-3-phenylpropanamido) ethyl carbamic acid benzyl ester

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