Acetic Acid → Ammonia

A mixture of (S)-(+)-1-amino-2-propanol (9 g, 0.12 mol), p-anisaldehyde (5.45 g, 0.04 mol), acetic acid (5 ml), and sodium triacetoxyborohydride (9.5 g, 0.045 mol) in methanol (80 ml) was stirred at room temperature for 72 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (150 ml) and sodium hydroxide solution (100 ml, 0.5N). The layers were separated, and the aqueous phase was extracted with further dichloromethane (4×30 ml). The combined organic solutions were dried (MgSO4) and concentrated under reduced pressure. The residual yellow oil was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (98:2:0.2 to 95:5:0.5) to afford the title compound, 6.2 g. 1H-NMR (CDCl3, 400MHz) δ: 1.10 (d, 3H), 2.24-2.40 (m, 2H), 2.65 (dd, 1H), 3.62-3.80 (m, 6H), 6.82 (d, 2H), 7.19 (d, 2H). LRMS: m/z (ES+) 218 [MNa+]

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. customthe residue was partitioned between dichloromethane (150 ml) and sodium hydroxide solution (100 ml, 0.5N)
3. customThe layers were separated
4. extractionthe aqueous phase was extracted with further dichloromethane (4×30 ml)
5. dry with materialThe combined organic solutions were dried (MgSO4)
6. concentrationconcentrated under reduced pressure
7. customThe residual yellow oil was purified by column chromatography on silica gel using an elution gradient of dichloromethane

ORD record

ord-4de19779c6e64e24a7b303f7705a2ea6

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06958402B2