(S)-Bis(3,5-dimethylphenyl)(pyrrolidin-2-yl)methanol

Base Information

• Chemical Name: (S)-Bis(3,5-dimethylphenyl)(pyrrolidin-2-yl)methanol
• CAS No.: 131180-63-7
• Molecular Formula: C21H27 N O
• Molecular Weight: 309.451
• European Community (EC) Number: 634-158-2
• DSSTox Substance ID: DTXSID50469527
• Nikkaji Number: J1.907.381E
• Wikidata: Q76421768
• Mol file: 131180-63-7.mol

Synonyms:131180-63-7;(S)-Bis(3,5-dimethylphenyl)(pyrrolidin-2-yl)methanol;(S)-alpha,alpha-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol;Bis(3,5-dimethylphenyl)-[(2S)-pyrrolidin-2-yl]methanol;(S)-(-)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine;2-Pyrrolidinemethanol, alpha,alpha-bis(3,5-dimethylphenyl)-, (2S)-;SCHEMBL9231480;DTXSID50469527;AKOS025294290;DS-13444;CS-0085703;J-005954;Bis(3,5-dimethylphenyl)[(2S)-pyrrolidin-2-yl]methanol;(S)- alpha , alpha -Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol;(S)-alpha,alpha-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol, >=99% (HPLC)

Chemical Property of (S)-Bis(3,5-dimethylphenyl)(pyrrolidin-2-yl)methanol

Chemical Property:

• Melting Point: 98-101 °C
• Boiling Point: 488.2±35.0 °C(Predicted)
• PKA: 13.70±0.29(Predicted)
• PSA: 32.26000
• Density: 1.068±0.06 g/cm3(Predicted)
• LogP: 4.23690
• Storage Temp.: 2-8°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 309.209264485
• Heavy Atom Count: 23
• Complexity: 349

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol ≥99% (HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)C(C2CCCN2)(C3=CC(=CC(=C3)C)C)O)C
• Isomeric SMILES: CC1=CC(=CC(=C1)C([C@@H]2CCCN2)(C3=CC(=CC(=C3)C)C)O)C
• Uses: (S)-α,α-Bis(3,5-dimethylphenyl)-2-pyrrolidinemethanol can be used as: A chiral organocatalyst in the preparation of α-[(phenyl)methyl]thio]alkanal derivatives using aldehydes as starting materials and [(phenyl)methyl]thio]triazole as a sulfur electrophile. A catalyst in the preparation of chiral bipyrazolidin-3-one derivatives by cycloadditions of azomethine imines with α,β-unsaturated aldehydes.

Technology Process of (S)-Bis(3,5-dimethylphenyl)(pyrrolidin-2-yl)methanol

There total 6 articles about (S)-Bis(3,5-dimethylphenyl)(pyrrolidin-2-yl)methanol 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: 92.0%

N-benzyl-(S)-bis(3,5-dimethylphenyl)(pyrrolidin-2-yl)methanol → bis(3,5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol (131180-63-7)

Guidance literature:

With hydrogen; acetic acid; palladium dihydroxide; In methanol; dichloromethane; at 20 ℃; under 760 Torr;

DOI:10.1021/ja028666b

Reference yield: 60.0%

3,5-dimethyphenylmagnesium bromide (34696-73-6) + (S)-proline-N-carboxyanhydride (45736-33-2) → bis(3,5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol (131180-63-7)

Guidance literature:

In tetrahydrofuran;

DOI:10.1021/jo00002a049

Reference yield:

5-bromo-1,3-xylene (556-96-7) → bis(3,5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol (131180-63-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: magnesium / tetrahydrofuran / 20 °C

1.2: 92 percent / tetrahydrofuran / 20 °C

2.1: 92 percent / H₂; acetic acid / Pd(OH)2/C / CH₂Cl₂; methanol / 20 °C / 760 Torr

With hydrogen; magnesium; acetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja028666b

upstream raw materials:

3,5-dimethyphenylmagnesium bromide

(S)-proline-N-carboxyanhydride

L-proline

5-bromo-1,3-xylene

Downstream raw materials:

(S)-2-{bis(3,5-dimethylphenyl)[(trimethylsilanyl)oxy]methyl}pyrrolidine

C₂₇H₂₉N₂O₂Cl