(R)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl-2-bromo-2-methyl propanoate

Base Information

• Chemical Name: (R)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl-2-bromo-2-methyl propanoate
• CAS No.: 1390644-50-4
• Molecular Formula: C₂₆H₃₆BrNO₃
• Molecular Weight: 490.481
• Mol file: 1390644-50-4.mol

Synonyms:(R)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl-2-bromo-2-methyl propanoate

Chemical Property of (R)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl-2-bromo-2-methyl propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl-2-bromo-2-methyl propanoate

There total 22 articles about (R)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl-2-bromo-2-methyl propanoate 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:

2-bromo-2-methylpropionyl chloride (20469-89-0) + (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol (207679-81-0) → (R)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl-2-bromo-2-methyl propanoate (1390644-50-4)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 0 - 5 ℃; for 0.5h; Inert atmosphere;

Reference yield:

Cinnamic acid (621-82-9) → (R)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl-2-bromo-2-methyl propanoate (1390644-50-4)

Guidance literature:

Multi-step reaction with 6 steps

1: sulfuric acid; acetic acid / 16 h / 100 °C

2: acetone / 2 h / 25 - 35 °C

3: boron trifluoride diethyl etherate / tetrahydrofuran / 1 h / -20 °C

4: hydrogen / 5%-palladium/activated carbon / methanol / 18 h / 25 - 35 °C / 2942.29 Torr / autoclave

5: potassium carbonate / acetone / 6 h / Reflux

6: sodium hydrogencarbonate / dichloromethane; water / 0.5 h / 0 - 5 °C / Inert atmosphere

With sulfuric acid; boron trifluoride diethyl etherate; hydrogen; sodium hydrogencarbonate; potassium carbonate; acetic acid; 5%-palladium/activated carbon; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

Reference yield:

(+/-)-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropane-1-ol → (R)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl-2-bromo-2-methyl propanoate (1390644-50-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 5 °C

2.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere

3.1: isopropyl alcohol / 30 - 55 °C

4.1: sodium hydroxide; water / dichloromethane / 0.25 h / 10 - 20 °C / pH 11.5

4.2: 4 h / 25 - 55 °C / Inert atmosphere

4.3: -70 - -10 °C / Inert atmosphere

5.1: thionyl chloride / 5 h / 40 - 45 °C

6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 0 - 5 °C / Inert atmosphere

7.1: hydrogen / 5%-palladium/activated carbon / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr

8.1: sodium hydrogencarbonate / dichloromethane; water / 0.5 h / 0 - 5 °C / Inert atmosphere

With dmap; thionyl chloride; water; hydrogen; sodium hydrogencarbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium hydroxide; 5%-palladium/activated carbon; In methanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile;

upstream raw materials:

methyl 4-(benzyloxy)-3-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]benzoate

2-bromo-2-methylpropionyl chloride

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

(R)-(-)-3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzoic acid methyl ester

Downstream raw materials:

fesoterodine

fesoterodine fumarate

isobutyric acid 2-((R)-3-diisopropylammonium-1-phenyIpropyl)-4-(hydroxymethyl)phenyl ester (R)-acetoxy(phenyl)acetate