(S)-(-)-1-[4,4-bisbenzyl-2-((diphenylphosphino)methyl)pyrrolidinyl]-2,2-dimethylpropan-1-one

Base Information

• Chemical Name: (S)-(-)-1-[4,4-bisbenzyl-2-((diphenylphosphino)methyl)pyrrolidinyl]-2,2-dimethylpropan-1-one
• CAS No.: 212890-82-9
• Molecular Formula: C₃₆H₄₀NOP
• Molecular Weight: 533.693
• Mol file: 212890-82-9.mol

Synonyms:(S)-(-)-1-[4,4-bisbenzyl-2-((diphenylphosphino)methyl)pyrrolidinyl]-2,2-dimethylpropan-1-one

Chemical Property of (S)-(-)-1-[4,4-bisbenzyl-2-((diphenylphosphino)methyl)pyrrolidinyl]-2,2-dimethylpropan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(-)-1-[4,4-bisbenzyl-2-((diphenylphosphino)methyl)pyrrolidinyl]-2,2-dimethylpropan-1-one

There total 10 articles about (S)-(-)-1-[4,4-bisbenzyl-2-((diphenylphosphino)methyl)pyrrolidinyl]-2,2-dimethylpropan-1-one 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: 96.0%

pivaloyl chloride (3282-30-2) + (S)-(-)-tert-butyl 4,4-bisbenzyl-2-[(diphenylphosphino)methyl]pyrrolidinecarboxylate (212890-93-2) → (S)-(-)-1-[4,4-bisbenzyl-2-((diphenylphosphino)methyl)pyrrolidinyl]-2,2-dimethylpropan-1-one (212890-82-9)

Guidance literature:

(S)-(-)-tert-butyl 4,4-bisbenzyl-2-[(diphenylphosphino)methyl]pyrrolidinecarboxylate; With hydrogenchloride; In 1,4-dioxane; at 0 - 20 ℃; for 2h;

pivaloyl chloride; With triethylamine; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1016/S0040-4020(98)00485-2

Reference yield: 75.0%

pivaloyl chloride (3282-30-2) + (S)-3,3-Dibenzyl-5-[(diphenylphosphanyl)-methyl]-pyrrolidin-2-one (627503-57-5) → (S)-(-)-1-[4,4-bisbenzyl-2-((diphenylphosphino)methyl)pyrrolidinyl]-2,2-dimethylpropan-1-one (212890-82-9)

Guidance literature:

(S)-3,3-Dibenzyl-5-[(diphenylphosphanyl)-methyl]-pyrrolidin-2-one; With lithium aluminium tetrahydride; In tetrahydrofuran; Heating;

pivaloyl chloride; With triethylamine; In ethyl acetate; at 20 ℃;

DOI:10.1021/jo035234q

Reference yield:

(5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane (99208-71-6) → (S)-(-)-1-[4,4-bisbenzyl-2-((diphenylphosphino)methyl)pyrrolidinyl]-2,2-dimethylpropan-1-one (212890-82-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi; HMDS / hexane; tetrahydrofuran / 20 °C

1.2: 94 percent / n-BuLi; HMDS; HMPA / hexane; tetrahydrofuran / 20 °C

2.1: 97 percent / p-TsOH*H₂O / methanol / Heating

3.1: 85 percent / dioxane; tetrahydrofuran / 0 °C

4.1: LiAlH₄ / tetrahydrofuran / Heating

4.2: 75 percent / Et₃N / ethyl acetate / 20 °C

With lithium aluminium tetrahydride; n-butyllithium; toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; 1,4-dioxane; methanol; hexane;

DOI:10.1021/jo035234q

upstream raw materials:

pivaloyl chloride

(S)-(-)-tert-butyl 4,4-bisbenzyl-2-[(diphenylphosphino)methyl]pyrrolidinecarboxylate

(S)-3,3-Dibenzyl-5-[(diphenylphosphanyl)-methyl]-pyrrolidin-2-one

benzyl bromide

Downstream raw materials:

C₈H₁₂Rh(P(C₆H₅)2CH₂CHCH₂C(CH₂C₆H₅)2CH₂NC(O)C(CH₃)3)⁽¹⁺⁾*SbF₆^(1-)=C₈H₁₂Rh(P(C₆H₅)2CH₂CHCH₂C(CH₂C₆H₅)2CH₂NC(O)C(CH₃)3)SbF₆