Benzaldehyde → (2R,3R)-3-(benzylamino)pentan-2-ol

To a solution of (2R,3R)-3-aminopentan-2-ol hydrochloride (1.00 g, 7.2 mmol) in DCM (20 mL) at rt was added sodium bicarbonate solution (604 mg, 7.2 mmol dissolved in 3.0 mL of water), dropwise. The reaction mixture was stirred for 1 hour, and the solvent was evaporated under reduced pressure. The residue and sodium cyanoborohydride (600 mg, 10.7 mmol) were added to a solution of benzyaldehyde 877 mg, 8.6 mmol) in DCM (20 mL). The reaction mixture was stirred at room temperature overnight and then concentrated in vacuo. 30.0 mL water was added to this mixture, and the aqueous layer was extracted with dichloromethane (3×10 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the residue on a silica gel column (0 to 50% EtOAc/hexanes) afforded (2R,3R)-3-(benzylamino)pentan-2-ol. MS APCl calc'd for C12H19NO [M+H]+ 194. found 194.

1. customthe solvent was evaporated under reduced pressure
2. stirringThe reaction mixture was stirred at room temperature overnight
3. concentrationconcentrated in vacuo
4. addition30.0 mL water was added to this mixture
5. extractionthe aqueous layer was extracted with dichloromethane (3×10 mL)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customPurification of the residue on a silica gel column (0 to 50% EtOAc/hexanes)

ORD record

ord-d8714113189b44da95a201fdeadf34c1

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846657B2