Benzoic acid (S)-((3R,4S)-1-methyl-2-oxo-4-vinyl-pyrrolidin-3-yl)-phenyl-methyl ester

Base Information

• Chemical Name: Benzoic acid (S)-((3R,4S)-1-methyl-2-oxo-4-vinyl-pyrrolidin-3-yl)-phenyl-methyl ester
• CAS No.: 891847-05-5
• Molecular Formula: C₂₁H₂₁NO₃
• Molecular Weight: 335.403

Synonyms:Benzoic acid (S)-((3R,4S)-1-methyl-2-oxo-4-vinyl-pyrrolidin-3-yl)-phenyl-methyl ester

Chemical Property of Benzoic acid (S)-((3R,4S)-1-methyl-2-oxo-4-vinyl-pyrrolidin-3-yl)-phenyl-methyl ester

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Technology Process of Benzoic acid (S)-((3R,4S)-1-methyl-2-oxo-4-vinyl-pyrrolidin-3-yl)-phenyl-methyl ester

There total 3 articles about Benzoic acid (S)-((3R,4S)-1-methyl-2-oxo-4-vinyl-pyrrolidin-3-yl)-phenyl-methyl 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:

4-methylamino-but-2-enyl benzoate (892848-68-9) → Benzoic acid (S)-((3R,4S)-1-methyl-2-oxo-4-vinyl-pyrrolidin-3-yl)-phenyl-methyl ester (891847-05-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / DCC; DMAP / CH₂Cl₂ / cooling

2.1: (S)-pymox-Ph / palladium(II) acetate / CH₂Cl₂ / 60 °C

2.2: NaBH₄ / methanol / cooling

3.1: pyridine; DMAP / 10 h / 20 °C

With pyridine; dmap; (S)-pymox-Ph; dicyclohexyl-carbodiimide; palladium diacetate; In dichloromethane;

DOI:10.1021/jo060288w

Reference yield:

N-methyl N-(Z)-(4'-benzoyloxy-2'-butenyl)-3-phenylpropynamide (891847-01-1) → Benzoic acid (S)-((3R,4S)-1-methyl-2-oxo-4-vinyl-pyrrolidin-3-yl)-phenyl-methyl ester (891847-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (S)-pymox-Ph / palladium(II) acetate / CH₂Cl₂ / 60 °C

1.2: NaBH₄ / methanol / cooling

2.1: pyridine; DMAP / 10 h / 20 °C

With pyridine; dmap; (S)-pymox-Ph; palladium diacetate; In dichloromethane;

DOI:10.1021/jo060288w

Reference yield:

(3R,4S)-3-((S)-Hydroxy-phenyl-methyl)-1-methyl-4-vinyl-pyrrolidin-2-one (891847-04-4) + benzoyl chloride (98-88-4) → Benzoic acid (S)-((3R,4S)-1-methyl-2-oxo-4-vinyl-pyrrolidin-3-yl)-phenyl-methyl ester (891847-05-5)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 10h;

DOI:10.1021/jo060288w

upstream raw materials:

(3R,4S)-3-((S)-Hydroxy-phenyl-methyl)-1-methyl-4-vinyl-pyrrolidin-2-one

benzoyl chloride

4-methylamino-but-2-enyl benzoate

N-methyl N-(Z)-(4'-benzoyloxy-2'-butenyl)-3-phenylpropynamide

Downstream raw materials:

isocynodine

Benzoic acid (S)-((3R,4S)-4-formyl-1-methyl-2-oxo-pyrrolidin-3-yl)-phenyl-methyl ester

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