Aluminium lithium hydride → (3S)-3-(Propan-2-yl)morpholine

To ice-cold THF (6 mL) was added lithium aluminum hydride (1.0 M solution in THF, 18.0 mL, 18.0 mmol). Once the addition was complete, a solution of (S)-5-isopropylmorpholin-3-one (1.3 g, 9.0 mmol) in THF (6 mL) was added dropwise over 20 min. Once the addition was completed, the ice bath was removed and the reaction mixture stirred at reflux for 18 h. The reaction was cooled in an ice-bath and to this was slowly added H2O (0.75 mL), then a 15% aqueous solution of NaOH (0.75 mL), and then H2O (0.75 mL). The resulting mixture was stirred at room temperature for 1 h and then filtered washing the solid with EtOAc (50 mL). The filtrate was concentrated at room temperature under reduced pressure to provide (S)-3-isopropylmorpholine (0.96 g, 83%) as a clear, colorless oil. 1H NMR and MS consistent.

1. additionOnce the addition
2. additionOnce the addition
3. customthe ice bath was removed
4. temperatureat reflux for 18 h
5. temperatureThe reaction was cooled in an ice-bath
6. stirringThe resulting mixture was stirred at room temperature for 1 h
7. filtrationfiltered
8. washwashing the solid with EtOAc (50 mL)
9. concentrationThe filtrate was concentrated at room temperature under reduced pressure

ORD record

ord-d1f917648eb147ca8512badbe86381d5

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863271B2