1-Amino-2-propanol → HCID 69157028, compound

To a solution (100 ml) of 4-formylbenzoic acid methyl ester (10.0 g) and (±)-1-amino-2-propanol (4.6 g) in THF was added anhydrous magnesium sulfate (11.2 g) at room temperature and the mixture was stirred for 3 hrs. The reaction mixture was filtered, and methanol (100 ml) was added to the filtrate under ice-cooling. Sodium borohydride (4.6 g) was added and the mixture was stirred for 1 hr. The reaction mixture was allowed to warm to room temperature and stirred for 12 hrs. and concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained crystal was washed with diisopropyl ether to give the title compound (8.5 g).

1. filtrationThe reaction mixture was filtered
2. additionmethanol (100 ml) was added to the filtrate under ice-
3. temperaturecooling
4. additionSodium borohydride (4.6 g) was added
5. stirringthe mixture was stirred for 1 hr
6. stirringstirred for 12 hrs
7. concentrationand concentrated under reduced pressure
8. additionTo the residue was added saturated aqueous sodium hydrogen carbonate
9. extractionthe mixture was extracted with methylene chloride
10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
11. customthe solvent was evaporated under reduced pressure
12. washThe obtained crystal was washed with diisopropyl ether

ORD record

ord-ed4754b6f74a470593babc1b7ecbcfd2

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402595B2