(S)-3-Methyl-2-phenylbutylamine

Base Information

• Chemical Name: (S)-3-Methyl-2-phenylbutylamine
• CAS No.: 106498-32-2
• Molecular Formula: C11H17N
• Molecular Weight: 163.263
• Mol file: 106498-32-2.mol

Synonyms:Benzeneethanamine,b-(1-methylethyl)-, (S)-;(+)-2-Phenyl-3-methylbutylamine;(S)-3-Methyl-2-phenylbutylamine;(S)-b-Isopropylphenethylamine;

Chemical Property of (S)-3-Methyl-2-phenylbutylamine

Chemical Property:

• Boiling Point: 236.278 °C at 760 mmHg
• PKA: 9.98±0.17(Predicted)
• Flash Point: 99.083 °C
• PSA: 26.02000
• Density: 0.925 g/cm³
• LogP: 3.08520

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-β-Isopropylphenethylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate in the process for producing optically active Flurbiprofen (F598700).

Technology Process of (S)-3-Methyl-2-phenylbutylamine

There total 9 articles about (S)-3-Methyl-2-phenylbutylamine 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:

(R)-3-Methyl-2-phenylbutylazid → (S)-3-methyl-2-phenylbutylamine (106498-32-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; Heating;

DOI:10.1016/S0957-4166(03)00454-3

Reference yield:

ethyl (E)-1-phenylbut-1-en-3-ol (36004-04-3) → (S)-3-methyl-2-phenylbutylamine (106498-32-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 41 percent / Burkholderia cepacia lipase / various solvent(s) / 24 h / 20 °C / Enzymatic reaction

2.1: 93 percent / KOH / methanol

3.1: propionic acid / 140 °C

3.2: 85 percent / NaOH / ethanol / Heating

4.1: 72 percent / LiAlH₄ / tetrahydrofuran

5.1: p-TsCl; pyridine

5.2: 67 percent / LiAlH₄ / tetrahydrofuran / Heating

6.1: O₃ / methanol; CH₂Cl₂ / -78 °C

6.2: 79 percent / NaBH₄ / methanol; CH₂Cl₂ / -78 °C

7.1: p-TsCl; pyridine

7.2: NaN₃ / aq. ethanol / 10 h / Heating

8.1: LiAlH₄ / diethyl ether / Heating

With pyridine; Burkholderia cepacia lipase; potassium hydroxide; lithium aluminium tetrahydride; ozone; propionic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3.1: Johnson-Claisen rearrangement;

DOI:10.1016/S0957-4166(03)00454-3

Reference yield:

(2R,3E)-4-phenyl-3-buten-2-ol (62413-47-2) → (S)-3-methyl-2-phenylbutylamine (106498-32-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: propionic acid / 140 °C

1.2: 85 percent / NaOH / ethanol / Heating

2.1: 72 percent / LiAlH₄ / tetrahydrofuran

3.1: p-TsCl; pyridine

3.2: 67 percent / LiAlH₄ / tetrahydrofuran / Heating

4.1: O₃ / methanol; CH₂Cl₂ / -78 °C

4.2: 79 percent / NaBH₄ / methanol; CH₂Cl₂ / -78 °C

5.1: p-TsCl; pyridine

5.2: NaN₃ / aq. ethanol / 10 h / Heating

6.1: LiAlH₄ / diethyl ether / Heating

With pyridine; lithium aluminium tetrahydride; ozone; propionic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.1: Johnson-Claisen rearrangement;

DOI:10.1016/S0957-4166(03)00454-3

upstream raw materials:

ethyl (E)-1-phenylbut-1-en-3-ol

(2R,3E)-4-phenyl-3-buten-2-ol

(R,E)-4-phenyl-3-buten-2-yl acetate

(2S)-3-methyl-2-phenylbutan-1-ol

Downstream raw materials:

(S)-3-methyl-2-phenylbutylammonium (R)-2-hydroxy-4-phenylbutanoate

Refernces

• 1、 -. "Process for optically resolving 2-(3-benzoylphenyl) propionic acid". . . Retrieved 2008/06/13.