Hydrochloric Acid → (2-Amino-9H-fluoren-9-yl)methanol

13.0 g 9-Hydroxymethyl-2-(Boc-amino)fluorene was dissolved in 110 ml acetonitrile and stirred under reflux. 42 ml 2 N HCl (2.0 equiv, 84 mmol) was added drop-wise. The reaction mixture was stirred under reflux for 45 min. The reaction mixture was cooled to room temperature and the reaction was monitored by TLC [Rf=0.1 PE-MTBE (1:2)]. The solvent was partially eliminated by rotary evaporation and the residue was dissolved in 70 ml 2 N HCl. The solution was carefully washed with 2×50 ml MTBE. The aqueous phase was adjusted to pH 9 by Na2CO3 and extracted with 2×70 ml EtOAc. The organic phase was washed with 50 ml brine and dried over Na2SO4. The solvent was eliminated by rotary evaporation. The product was used without further purification. The structural identity was verified by NMR (8.76 g, 99% yield).

1. temperatureunder reflux
2. stirringThe reaction mixture was stirred
3. temperatureunder reflux for 45 min
4. customThe solvent was partially eliminated by rotary evaporation
5. dissolutionthe residue was dissolved in 70 ml 2 N HCl
6. washThe solution was carefully washed with 2×50 ml MTBE
7. extractionextracted with 2×70 ml EtOAc
8. washThe organic phase was washed with 50 ml brine
9. dry with materialdried over Na2SO4
10. customThe solvent was eliminated by rotary evaporation
11. customThe product was used without further purification

ORD record

ord-48256a2325c3432eb528827879aa9a12

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871949B2