Water → HCID 98601535, Verbindung

Prepared according to US patent: 20070032433A1. To a solution of (R)-5-(hydroxymethyl)-3,3-dimethylpyrrolidin-2-one (2.91 g, 20.30 mmol) in THF (50.8 mL) cooled to 0° C., lithium aluminum hydride (2.0 M solution in THF, 12.18 mL, 24.36 mmol) was added. The mixture was stirred at room temperature overnight (16 h). Additional lithium aluminum hydride (2.0 M solution in THF, 12.18 mL, 24.36 mmol) was added and the solution was refluxed for 6 h. The reaction mixture was cooled and additional lithium aluminum hydride (2.0 M solution in THF, 12.18 mL, 24.36 mmol) was added and the mixture was refluxed overnight. The reaction mixture was cooled to 0° C. in an ice bath prior to addition of water (3.67 mL) followed by 15% aqueous NaOH (3.67 mL) and water (10.9 mL). It was then stir vigorously at room temperature for 1 h and filtered on a medium porosity sintered glass frit with cotton and celite washing with EtOAc. The solution was then concentrated affording crude (R)-(4,4-dimethylpyrrolidin-2-yl)methanol (2.29 g, 17.73 mmol, 87% yield) as yellow viscous oil. MS (ESI) 130.1 [M+H]+.

1. customPrepared
2. temperaturethe solution was refluxed for 6 h
3. temperatureThe reaction mixture was cooled
4. temperaturethe mixture was refluxed overnight
5. temperatureThe reaction mixture was cooled to 0° C. in an ice bath
6. stirringIt was then stir vigorously at room temperature for 1 h
7. filtrationfiltered on a medium porosity sintered glass frit with cotton and celite
8. washwashing with EtOAc
9. concentrationThe solution was then concentrated

ORD-Eintrag

ord-d3f3b95ffd9242608daaf65dee352ac4

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09365522B2