1-Pyrrolidinepropanol, β-amino-α-(2,3-dihydro-1,4-benzodioxin-6-yl)-, (αR,βR)-

Base Information

• Chemical Name: 1-Pyrrolidinepropanol, β-amino-α-(2,3-dihydro-1,4-benzodioxin-6-yl)-, (αR,βR)-
• CAS No.: 491833-28-4
• Molecular Formula: C₁₅H₂₂N₂O₃
• Molecular Weight: 278.351
• Mol file: 491833-28-4.mol

Synonyms:(1R,2R)-2-amino-1-(2,3-dihydrobenzo[β][1,4]dioxin-6-yl)-3-pyrrolidin-1-yl-propan-1-ol

Chemical Property of 1-Pyrrolidinepropanol, β-amino-α-(2,3-dihydro-1,4-benzodioxin-6-yl)-, (αR,βR)-

Chemical Property:

• Boiling Point: 471.2±45.0 °C(Predicted)
• PKA: 11.75±0.45(Predicted)
• Density: 1.232±0.06 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

(1R,2R)-2-Amino-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(pyrrolidin-1-yl)propan-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: 1-Pyrrolidinepropanol, β-amino-α-(2,3-dihydro-1,4-benzodioxin-6-yl)-, (αR,βR)-, also known as eliglustat, is a potent and selective glucosylceramide synthase (GCS) inhibitor used in the treatment of type 1 Gaucher disease. Its synthesis has been optimized through various methods, including diastereoselective aldol reactions, ruthenium(II)-catalyzed asymmetric transfer hydrogenation, and scalable processes that ensure high stereoselectivity (>99.9% de and ee) and overall yield. 1-Pyrrolidinepropanol, β-amino-α-(2,3-dihydro-1,4-benzodioxin-6-yl)-, (αR,βR)-'s therapeutic efficacy stems from its ability to reduce glucosylceramide accumulation, addressing the underlying pathology of glycosphingolipid storage disorders.

Technology Process of 1-Pyrrolidinepropanol, β-amino-α-(2,3-dihydro-1,4-benzodioxin-6-yl)-, (αR,βR)-

There total 59 articles about 1-Pyrrolidinepropanol, β-amino-α-(2,3-dihydro-1,4-benzodioxin-6-yl)-, (αR,βR)- 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: 98.0%

(1R,2R)-2-amino-1-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-3-pyrrolidin-1-yl-propan-1-ol dioxalate salt → (1R,2R)-2-amino-1-(2,3-dihydrobenzo[β][1,4]dioxin-6-yl)-3-pyrrolidin-1-yl-propan-1-ol (491833-28-4)

Guidance literature:

With sodium hydroxide; In water; at 5 - 20 ℃; pH=14;

Reference yield: 97.7%

1-((2R,3R)-2-azido-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-hydroxypropyl)pyrrolidine → (1R,2R)-2-amino-1-(2,3-dihydrobenzo[β][1,4]dioxin-6-yl)-3-pyrrolidin-1-yl-propan-1-ol (491833-28-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 5h; under 912.061 Torr;

Reference yield: 90.0%

(1R,2R,1''S)-1-(2',3'-dihydro-benzo[1,4]dioxin-6'-yl)-2-(2''-hydroxy-1''-phenyl-ethylamino)-3-pyrrolidin-1-yl-propan-1-ol → (1R,2R)-2-amino-1-(2,3-dihydrobenzo[β][1,4]dioxin-6-yl)-3-pyrrolidin-1-yl-propan-1-ol (491833-28-4)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; trifluoroacetic acid; In methanol; water; at 20 ℃; under 5171.62 - 6205.94 Torr; Pressure; Temperature; Reagent/catalyst; Inert atmosphere;

upstream raw materials:

tert-butyl ((1R,2R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)carbamate

tert-butyl ((1R,2R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1,3-dihydroxypropan-2-yl)carbamate

(2R,3R)-2-((tert-butoxycarbonyl)amino)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-hydroxypropyl methanesulfonate

(1R,3S,5S,8aS)-1,3-bis(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-phenyltetrahydro-3H,8H-oxazolo[4,3-c][1 ,4]oxazin-8-one

Downstream raw materials:

(1R,2R)-octanoic acid [2-(2',3'-dihydro-benzo[1,4]dioxin-6'-yl)-2-hydroxy-1-pyrrolidin-1-ylmethyl-ethyl]-amide

eliglustat

D-threo-1-(3',4'-ethylenedioxy)phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol