(S_P,S_C)-{2-[(diphenylphosphinyl)methyl]pyrrolidin-1-yl}-2-[(1-naphthyl)phenylphosphinyl]ethanone

Base Information

• Chemical Name: (S_P,S_C)-{2-[(diphenylphosphinyl)methyl]pyrrolidin-1-yl}-2-[(1-naphthyl)phenylphosphinyl]ethanone
• CAS No.: 871246-61-6
• Molecular Formula: C₃₅H₃₃NOP₂
• Molecular Weight: 545.601

Synonyms:(S_P,S_C)-{2-[(diphenylphosphinyl)methyl]pyrrolidin-1-yl}-2-[(1-naphthyl)phenylphosphinyl]ethanone

Chemical Property of (S_P,S_C)-{2-[(diphenylphosphinyl)methyl]pyrrolidin-1-yl}-2-[(1-naphthyl)phenylphosphinyl]ethanone

Chemical Property:

Purity/Quality:

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Technology Process of (S_P,S_C)-{2-[(diphenylphosphinyl)methyl]pyrrolidin-1-yl}-2-[(1-naphthyl)phenylphosphinyl]ethanone

There total 8 articles about (S_P,S_C)-{2-[(diphenylphosphinyl)methyl]pyrrolidin-1-yl}-2-[(1-naphthyl)phenylphosphinyl]ethanone 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: 48.0%

(S)-1-naphthyl(phenyl)phosphinylacetic acid (871246-58-1) + (S)-(-)-2-(diphenylphosphino)methylpyrrolidine hydrochloride → (SP,SC)-{2-[(diphenylphosphinyl)methyl]pyrrolidin-1-yl}-2-[(1-naphthyl)phenylphosphinyl]ethanone (871246-61-6)

Guidance literature:

(S)-1-naphthyl(phenyl)phosphinylacetic acid; With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 ℃; for 1h;

(S)-(-)-2-(diphenylphosphino)methylpyrrolidine hydrochloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2005.09.136

Reference yield:

C17H15OP*BH3 → (SP,SC)-{2-[(diphenylphosphinyl)methyl]pyrrolidin-1-yl}-2-[(1-naphthyl)phenylphosphinyl]ethanone (871246-61-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₂SO₄ / methanol

1.2: H₂O

2.1: s-BuLi / cyclohexane; tetrahydrofuran / 2 h / -78 °C

2.2: cyclohexane; tetrahydrofuran / 3 h / -40 °C

3.1: TFA / CH₂Cl₂ / 2 h / 0 °C

3.2: 90 percent / aq. NaOH

4.1: EDC; DMAP / CH₂Cl₂ / 1 h / 0 °C

4.2: 48 percent / CH₂Cl₂ / 0 - 20 °C

With dmap; sulfuric acid; sec.-butyllithium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; cyclohexane;

DOI:10.1016/j.tetlet.2005.09.136

Reference yield:

(S)-Methyl-naphthalen-1-yl-phenyl-phosphane; compound with borane → (SP,SC)-{2-[(diphenylphosphinyl)methyl]pyrrolidin-1-yl}-2-[(1-naphthyl)phenylphosphinyl]ethanone (871246-61-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: s-BuLi / cyclohexane; tetrahydrofuran / 2 h / -78 °C

1.2: cyclohexane; tetrahydrofuran / 3 h / -40 °C

2.1: TFA / CH₂Cl₂ / 2 h / 0 °C

2.2: 90 percent / aq. NaOH

3.1: EDC; DMAP / CH₂Cl₂ / 1 h / 0 °C

3.2: 48 percent / CH₂Cl₂ / 0 - 20 °C

With dmap; sec.-butyllithium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1016/j.tetlet.2005.09.136

upstream raw materials:

(S)-1-naphthyl(phenyl)phosphinylacetic acid

bis(diethylamino)phenylphosphine

(4S,5R)-3,4-Dimethyl-2,5-diphenyl-[1,3,2]oxazaphospholidine

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