Acetic Acid → (2R)-2-(Benzylamino)propan-1-ol

Glacial HOAc (1.5 mL) was added dropwise at room temperature to a well stirred solution of (R)-(+)-2-amino-1-propanol (10.0 g, 133 mmol) and benzaldehyde (13.5 mL, 133 mmol) in CH3OH (260 mL). The reaction mixture was stirred at room temperature for 1.5 h followed by addition of NaCNBH3 (12.6 g, 200 mmol) and the reaction stirred at room temperature overnight. The reaction was concentrated under reduced pressure and the recovered solids dissolved in EtOAc (500 mL) and then washed with saturated bicarbonate (2×250 mL), H2O (250 mL) and saturated brine (250 mL). The organic phase was then dried over Na2SO4, filtered and concentrated to yield (R)-2-(benzylamino)propan-1-ol (19.8 g, 94%) as a colorless oil: MS consistent.

1. stirringthe reaction stirred at room temperature overnight
2. concentrationThe reaction was concentrated under reduced pressure
3. dissolutionthe recovered solids dissolved in EtOAc (500 mL)
4. washwashed with saturated bicarbonate (2×250 mL), H2O (250 mL) and saturated brine (250 mL)
5. dry with materialThe organic phase was then dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-869a907a2e6d4e67a2ac00115e7a923f

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863271B2