Aluminium lithium hydride → (R)-3-isopropylmorpholine

To ice-cold tetrahydrofuran (8.0 mL) was added lithium aluminum hydride (1.0 M solution in tetrahydrofuran, 23.0 mL, 23.0 mmol). Once the addition was complete, a solution of (R)-5-isopropylmorpholin-3-one (1.7 g, 12.0 mmol) in tetrahydrofuran (8 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 20 h. The reaction was cooled in an ice-bath and to this was slowly added water (1.0 mL), then a 15% solution of sodium hydroxide (1.0 mL), and then water (1.0 mL). The resulting mixture was stirred at room temperature for 1.5 h and then filtered washing the solid with ethyl acetate (50 mL). The filtrate was concentrated at room temperature under reduced pressure to provide (R)-3-isopropylmorpholine (1.4 g, 93%) as a light yellow oil. 1H NMR consistent.

1. additionOnce the addition
2. additionOnce the addition
3. customthe ice bath was removed
4. temperatureat reflux for 20 h
5. temperatureThe reaction was cooled in an ice-bath
6. stirringThe resulting mixture was stirred at room temperature for 1.5 h
7. filtrationfiltered
8. washwashing the solid with ethyl acetate (50 mL)
9. concentrationThe filtrate was concentrated at room temperature under reduced pressure

ORDレコード

ord-db4cfa34c0164711a110c238e752b5f0

出典データセット

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07863271B2