4-(2-(Benzyl(methyl)amino)-1-hydroxyethyl)-1,2-phenylene bis(2,2-dimethylpropanoate)

Base Information

• Chemical Name: 4-(2-(Benzyl(methyl)amino)-1-hydroxyethyl)-1,2-phenylene bis(2,2-dimethylpropanoate)
• CAS No.: 133789-72-7
• Molecular Formula: C₂₆H₃₅NO₅
• Molecular Weight: 441.568
• DSSTox Substance ID: DTXSID30564221
• Mol file: 133789-72-7.mol

Synonyms:133789-72-7;4-(2-(Benzyl(methyl)amino)-1-hydroxyethyl)-1,2-phenylene bis(2,2-dimethylpropanoate);[4-[2-[benzyl(methyl)amino]-1-hydroxyethyl]-2-(2,2-dimethylpropanoyloxy)phenyl] 2,2-dimethylpropanoate;4-{2-[Benzyl(methyl)amino]-1-hydroxyethyl}-1,2-phenylene bis(2,2-dimethylpropanoate);DTXSID30564221

Chemical Property of 4-(2-(Benzyl(methyl)amino)-1-hydroxyethyl)-1,2-phenylene bis(2,2-dimethylpropanoate)

Chemical Property:

• PSA: 76.07000
• LogP: 4.75500
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 441.25152322
• Heavy Atom Count: 32
• Complexity: 615

Purity/Quality:

4-(2-(Benzyl(methyl)amino)-1-hydroxyethyl)-1,2-phenylene bis(2,2-dimethylpropanoate) 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OC1=C(C=C(C=C1)C(CN(C)CC2=CC=CC=C2)O)OC(=O)C(C)(C)C

Technology Process of 4-(2-(Benzyl(methyl)amino)-1-hydroxyethyl)-1,2-phenylene bis(2,2-dimethylpropanoate)

There total 8 articles about 4-(2-(Benzyl(methyl)amino)-1-hydroxyethyl)-1,2-phenylene bis(2,2-dimethylpropanoate) 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:

pivaloyl chloride (3282-30-2) → (R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol (133789-72-7)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1002/hlca.19910740216

Reference yield:

4-formyl-1,2-phenylene bis(2,2-dimethylpropanoate) (84260-69-5) → (R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol (133789-72-7)

Guidance literature:

Multi-step reaction with 6 steps

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

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

3: 90 percent / ZnCl₂, DIBAL / tetrahydrofuran / 1 h / -78 °C

4: 65 percent / Al-Hg / tetrahydrofuran; H₂O / 12 h / Ambient temperature

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

6: tetrahydrofuran / 6 h

With manganese(IV) oxide; aluminium amalgam; trimethoxonium tetrafluoroborate; diisobutylaluminium hydride; potassium carbonate; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/hlca.19910740216

Reference yield:

(R)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>-2-(p-tolylsulfinyl)ethan-1-on (133789-69-2) → (R)-2-(N-benzyl-N-methylamino)-1-<3',4'-bis<(pivaloyl)oxy>phenyl>ethan-1-ol (133789-72-7)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 65 percent / Al-Hg / tetrahydrofuran; H₂O / 12 h / Ambient temperature

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

4: tetrahydrofuran / 6 h

With aluminium amalgam; trimethoxonium tetrafluoroborate; diisobutylaluminium hydride; potassium carbonate; zinc(II) chloride; In tetrahydrofuran; water;

DOI:10.1002/hlca.19910740216

upstream raw materials:

(R)-2-<3',4'-bis<(pivaloyl)oxy>phenyl>oxirane

benzyl-methyl-amine

pivaloyl chloride

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

Downstream raw materials:

(-)-(R)-3,4-di-O-pivaloylepinephrine hydrochloride

(+)-(S)-3,4-di-O-pivaloylepinephrine hydrochloride

Refernces