3-Amino-1-propanol → HCID 71489278, compound

To a solution of 3-Aminopropanol (5.00 kg, 66.6 mol) in acetonitrile (35 L) was added (S)—N-(1-methanesulfonyloxypropan-2-yl)-2-nitrobenzenesulfonamide (7.00 kg, 20.7 mol) was added at an internal temperature of 10° C. to 20° C. The reaction mixture was further stirred for 16 hours. After confirming the disappearance of the starting materials by TLC, the mixture was concentrated under reduced pressure. To the residue was added water. The resulting solution was acidified with 6 N hydrochloric acid until pH 4, and the insoluble materials were filtered off. The filtrate was made alkaline by adding potassium carbonate until pH 9 and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the target product as a pale yellow oil (6.10 kg, 92.8%).

1. additionwas added at an internal temperature of 10° C. to 20° C
2. concentrationthe mixture was concentrated under reduced pressure
3. additionTo the residue was added water
4. filtrationthe insoluble materials were filtered off
5. additionby adding potassium carbonate until pH 9
6. extractionextracted with ethyl acetate
7. washThe resulting organic layer was washed with saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-19191e8a090e4a148a1ba529c9b9a7f0

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045460B2