Benzaldehyde → (2R)-2-(Benzylamino)propan-1-ol

To (2R)-2-amino-1-propanol (4.5 g, 60 mmol) in toluene (120 mL) was added benzaldehyde (636 mL). A Dean-Stark trap was placed on the flask, and the reaction mixture was heated to reflux until no further water evolved. The reaction was cooled down to room temperature and concentrated. The resulting residue was dissolved in ethanol (120 mL), and treated with NaBH4 (5.67 g, 150 mmol) at 0° C. followed by sufficient 4N HCl in dioxane to adjust the pH to 2. The reaction mixture was stirred overnight at room temperature, and then concentrated in vacuo. The resulting residue was dissolved in 1N aq. HCl (200 mL) and washed with CH2Cl2 (2×100 mL). The aqueous phase was then adjusted to pH>13 with 6N aqueous NaOH and extracted with CH2Cl2 (2×150 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated to afford the title compound (9.44 g, 95%) as a colorless oil which solidified under high vacuum. LC-MS (ES) m/z=166.2 [M+H]+

1. temperaturethe reaction mixture was heated
2. concentrationconcentrated
3. dissolutionThe resulting residue was dissolved in ethanol (120 mL)
4. concentrationconcentrated in vacuo
5. dissolutionThe resulting residue was dissolved in 1N aq. HCl (200 mL)
6. washwashed with CH2Cl2 (2×100 mL)
7. extractionextracted with CH2Cl2 (2×150 mL)
8. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-4b277d8264b34250ae12d3620dab49c8

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697685B2