1-Pyrrolidinepropanol, β-amino-α-(2,3-dihydro-1,4-benzodioxin-6-yl)-, (αR,βR)- synthesis
- Product Name:1-Pyrrolidinepropanol, β-amino-α-(2,3-dihydro-1,4-benzodioxin-6-yl)-, (αR,βR)-
- CAS Number:491833-28-4
- Molecular formula:C15H22N2O3
- Molecular Weight:278.35
502483-57-0
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491833-28-4
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Yield:491833-28-4 0.8 g
Reaction Conditions:
with hydrogenchloride in dichloromethane;water at 25 - 50; for 6.75 h;
Steps:
18 Example-18: Preparation of (1R,2R)-2-amino-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(pyrrolidin-1-yl)propan-1-ol of formula (Xllb).
Tert-b ty ((IR, 2R)- 1 -(2,3-dihydrobenzo[b] [ 1 ,4]dioxin-6-yl)- 1 -hydroxy-3-(pyrrolidin- l-yl)propan-2-yl)carbamate (2.5 gms) was added to dichloromethane (25 ml) at 25-30°C. Hydrochloric acid (10 ml) was added to the mixture and stirred for 45 min. Heated the mixture to 45-50°C and stirred for 6 hrs. Cooled the reaction mixture to 30°C and separated the both aqueous and organic layers. The aqueous layer was extracted with dichloromethane. Basified the aqueous layer with aqueous sodium hydroxide solution and added dichloromethane (10 ml) and stirred for 15 min. Separated the organic and aqueous layers. Combined the total organic layers and distilled off the solvent completely from the organic layer under reduced pressure to get the title compound. (Yield: 0.8 gms).
References:
WO2019/82209,2019,A1 Location in patent:Page/Page column 30