Ethanol → 3-Isobutylamino-propan-1-ol

To a solution of 2-isopropyltetrahydro-1,3-oxazole (4.94 g, 38.2 mmol) in abs. EtOH (100 mL) at 0° C. was added NaBH4 (2.17 g (57.4 mmol, 1.5 equiv.) in small portions over 15 min. and the resulting mixture was stirred at room temp.overnight. The resulting mixture was concentrated under reduced pressure, then treated with EtOAc (150 mL) and water (100 mL) (CAUTION; gas evolution), and stirred at room temp for 30 min. The resulting organic layer was washed with a saturated NaCl solution. The combined aqueous layers were back-extracted with EtOAc (150 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford N-isobutyl-3-hydroxypropylamine as a colorless oil (5.04 g, 100%): 1H NMR (CDCl3) δ0.84 (d, J=6.6 Hz, 6H), 1.60-1.71 (m, 3H), 2.36 (d, J=6.6 Hz, 2H), 2.80 (dd, J=5.9, 5.9 Hz, 2H), 3.10-3.30 (br s, 2H), 3.74 (dd,, J=5.5, 5.5 Hz, 2H); 13C NMR (CDCl3) δ20.5, 28.1, 30.6, 50.0, 57.8, 64.1.

1. customovernight
2. concentrationThe resulting mixture was concentrated under reduced pressure
3. additiontreated with EtOAc (150 mL) and water (100 mL) (CAUTION; gas evolution)
4. stirringstirred at room temp for 30 min
5. washThe resulting organic layer was washed with a saturated NaCl solution
6. extractionThe combined aqueous layers were back-extracted with EtOAc (150 mL)
7. dry with materialThe combined organic layers were dried (Na2SO4)
8. concentrationconcentrated under reduced pressure

ORD record

ord-231816c226ec4f2f91b3440c9ecfd1ae

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06353006B1