(S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol

Base Information

• Chemical Name: (S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol
• CAS No.: 145549-09-3
• Molecular Formula: C₁₈H₂₁NO
• Molecular Weight: 267.371
• Mol file: 145549-09-3.mol

Synonyms:(S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol

Chemical Property of (S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol

There total 6 articles about (S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol 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: 94.0%

(3S,7R,7aR)-3,7-Diphenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one (145549-03-7) → (S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol (145549-09-3)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/jo00053a012

Reference yield:

(3S,7aR)-5-oxo-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole (122383-34-0) → (S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol (145549-09-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) lithium hexamethyldisilazane / 1.) THF, -78 deg C, 1 h, 2.) 15 min

2: 1.) phenylselenyl bromide, 2.) 30percent H₂O₂ / 1.) THF, 30 min, 2.) CH₂Cl₂, H₂O, a) 0 deg C, 30 min, b) 0 deg C to r.t., 30 min

3: 1.) CuCN / 1.) THF, cyclohexane, ether, -78 deg C to 0 deg C, 2.) THF, -78 deg C, 30 min

4: 1.) ammonium formate / 1.) 5percent Pd/C / 1.) MeOH, 1.5 h, 2.) toluene, reflux, 1.5 h

5: 94 percent / AlCl₃, LiAlH₄ / tetrahydrofuran / 1 h / -78 °C

With lithium aluminium tetrahydride; aluminium trichloride; Phenylselenyl bromide; dihydrogen peroxide; ammonium formate; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/jo00053a012

Reference yield:

phenyllithium (591-51-5) → (S)-2-Phenyl-2-((R)-3-phenyl-pyrrolidin-1-yl)-ethanol (145549-09-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) CuCN / 1.) THF, cyclohexane, ether, -78 deg C to 0 deg C, 2.) THF, -78 deg C, 30 min

2: 1.) ammonium formate / 1.) 5percent Pd/C / 1.) MeOH, 1.5 h, 2.) toluene, reflux, 1.5 h

3: 94 percent / AlCl₃, LiAlH₄ / tetrahydrofuran / 1 h / -78 °C

With lithium aluminium tetrahydride; aluminium trichloride; ammonium formate; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/jo00053a012

upstream raw materials:

(3S,7R,7aR)-3,7-Diphenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

(3S,7aR)-5-oxo-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole

phenyllithium

(3S,7aR)-5-Oxo-3-phenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester

Downstream raw materials:

tert-butyl (R)-3-phenylpyrrolidine-1-carboxylate

(-)-(R)-3-Phenylpyrrolidine

Refernces