Propanoic acid, 2,2-dimethyl-, 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester, hydrochloride, (S)-

Base Information

• Chemical Name: Propanoic acid, 2,2-dimethyl-, 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester, hydrochloride, (S)-
• CAS No.: 133815-41-5
• Molecular Formula: C₁₉H₂₉NO₅*ClH
• Molecular Weight: 387.904
• Mol file: 133815-41-5.mol

Synonyms:Propanoic acid, 2,2-dimethyl-, 4-[(1S)-1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester, hydrochloride;Propanoic acid, 2,2-dimethyl-, 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester, hydrochloride, (S)-

Chemical Property of Propanoic acid, 2,2-dimethyl-, 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester, hydrochloride, (S)-

Chemical Property:

• PSA: 84.86000
• LogP: 4.03530

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Propanoic acid, 2,2-dimethyl-, 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester, hydrochloride, (S)-

There total 10 articles about Propanoic acid, 2,2-dimethyl-, 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester, hydrochloride, (S)- 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)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol (133789-72-7) → (+)-(S)-3,4-di-O-pivaloylepinephrine hydrochloride (133815-41-5,64019-93-8) + (-)-(R)-3,4-di-O-pivaloylepinephrine hydrochloride (79071-01-5,64019-93-8)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; In ethanol; under 11400 Torr; Yield given. Yields of byproduct given;

DOI:10.1002/hlca.19910740216

Reference yield:

dipivefrin hydrochloride (64019-93-8) → (+)-(S)-3,4-di-O-pivaloylepinephrine hydrochloride (133815-41-5,64019-93-8) + (-)-(R)-3,4-di-O-pivaloylepinephrine hydrochloride (79071-01-5,64019-93-8)

Guidance literature:

With Chiralpak ID; In formic acid; hexane; diethylamine; isopropyl alcohol; at 25 ℃; enantioselective reaction; Resolution of racemate;

DOI:10.1039/C8NJ00685G

Reference yield:

pivaloyl chloride (3282-30-2) → (+)-(S)-3,4-di-O-pivaloylepinephrine hydrochloride (133815-41-5,64019-93-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / Et₃N / tetrahydrofuran / 3 h / 25 °C

2: 1.) LDA / 1.) 0 deg C, THF, 1 h 2.) -78 deg C, THF, 4 h

3: 80 percent / activated MnO₂ / CH₂Cl₂ / 2 h

4: 90 percent / ZnCl₂, DIBAL / tetrahydrofuran / 1 h / -78 °C

5: 65 percent / Al-Hg / tetrahydrofuran; H₂O / 12 h / Ambient temperature

6: 1.) Me₃OBF₄ 2.) K₂CO₃ / 1.) MeNO₂, 0 deg C, 1 h 2.) CH₂Cl₂, MeOH/H₂O, r. t.

7: tetrahydrofuran / 6 h

8: 10percent Pd-C, 1.2 N HCl / ethanol / 11400 Torr

With hydrogenchloride; manganese(IV) oxide; palladium on activated charcoal; aluminium amalgam; trimethoxonium tetrafluoroborate; diisobutylaluminium hydride; potassium carbonate; triethylamine; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1002/hlca.19910740216

upstream raw materials:

(R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol

pivaloyl chloride

4-formyl-1,2-phenylene bis(2,2-dimethylpropanoate)

(R)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>-2-(p-tolylsulfinyl)ethan-1-on

Refernces

• 1、 Solladie-Cavallo,Simon-Wermeister,Farkhani. "Enanthioselective synthesis of both enantioners of a isoproterenol analogue and of di-O-pivaloylepinephrine". . p. 390 - 396. Retrieved 2007/10/02.