Aluminium lithium hydride → HCID 118383118, compound

Temperature

75 °C

To a solution of (5R)-5-(hydroxymethyl)-3-isopropylpyrrolidin-2-one (2.251 g, 14.32 mmol) in THF (25 mL) was added lithium aluminium hydride, 1.0 M solution in THF (20.05 mL, 20.05 mmol) at room temperature dropwise slowly. The resulting mixture was then refluxed at 75° C. for 2 h. Additional lithium aluminium hydride, 1.0 M solution in THF (20.05 mL, 20.05 mmol) was added and the mixture was refluxed overnight. After 18 h, the reaction mixture was allowed to cool to 0° C. The reaction was quenched by adding saturated aqueous solution of Rochelle's salt. The reaction mixture was stirred vigorously for 1 h and the layers were separated. The aqueous layer was extracted with EtOAc twice and the organics were combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide ((2R)-4-isopropylpyrrolidin-2-yl)methanol (1.645 g, 11.49 mmol, 80% yield) as a light yellow oil. The crude material was used in the next step without further purification. m/z (ESI, +ve) 144 (M+H).

1. temperaturethe mixture was refluxed overnight
2. temperatureto cool to 0° C
3. customThe reaction was quenched
4. additionby adding saturated aqueous solution of Rochelle's salt
5. customthe layers were separated
6. extractionThe aqueous layer was extracted with EtOAc twice
7. washwashed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-07b4b5dcb0c54002a61b13dc7955de1e

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365522B2