(S)-2-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: (S)-2-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester
• CAS No.: 301222-30-0
• Molecular Formula: C₄₂H₅₃FN₄O₃
• Molecular Weight: 680.906

Synonyms:

Chemical Property of (S)-2-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester

Chemical Property:

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Technology Process of (S)-2-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester

There total 3 articles about (S)-2-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester 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:

2-bromo-2,3-dimethylbutanoic acid (106660-88-2) → (S)-2-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester (301222-30-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: AgOTf; DIEA / tetrahydrofuran / 20 °C

1.2: 60 percent / aq. TFA / tetrahydrofuran; acetonitrile / preparative RP-HPLC

2.1: Cs₂CO₃ / dimethylformamide / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

4.1: NaBH(OAc)3; DIEA / 1,2-dichloro-ethane

With oxalyl dichloride; silver trifluoromethanesulfonate; sodium tris(acetoxy)borohydride; caesium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 3.1: Swern oxidation;

DOI:10.1016/j.bmcl.2003.12.005

Reference yield:

(S)-2-[(3S,4R)-3-(3-Fluoro-phenyl)-4-hydroxymethyl-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester (301222-28-6) → (S)-2-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester (301222-30-0)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2: NaBH(OAc)3; DIEA / 1,2-dichloro-ethane

With oxalyl dichloride; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1,2-dichloro-ethane; 1: Swern oxidation;

DOI:10.1016/j.bmcl.2003.12.005

Reference yield:

4-(3-benzyl-1-ethyl-pyrazol-5-yl)piperidine (301219-18-1) + (S)-2-[(3S,4R)-3-(3-Fluoro-phenyl)-4-formyl-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester (301222-29-7) → (S)-2-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester (301222-30-0)

Guidance literature:

With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2003.12.005

upstream raw materials:

4-(3-benzyl-1-ethyl-pyrazol-5-yl)piperidine

(S)-2-[(3S,4R)-3-(3-Fluoro-phenyl)-4-formyl-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester

2-bromo-2,3-dimethylbutanoic acid

(S)-2-[(3S,4R)-3-(3-Fluoro-phenyl)-4-hydroxymethyl-pyrrolidin-1-yl]-2,3-dimethyl-butyric acid 4-methoxy-benzyl ester

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