Hydrochloric Acid → HCID 57463659, compound

To (S)-(+)-2-amino-1-propanol (19.6 g, 0.26 mol) dissolved in dichloromethane (500 ml) was added propionaldehyde (20.9 ml, 0.28 mol) followed by pre-dried powdered 4 A molecular sieves (40 g) and the mixture stirred at room temperature overnight. The mixture was filtered through a pad of celite, the pad washed with dichloromethane, and solvent evaporated to give a clear oil. This oil was dissolved in methanol (200 ml) and NaBH4 was added portionwise over 15 minutes. The mixture was stirred at room temperature overnight, then quenched by cautious addition of 2M HCl(aq) (200 ml), basified by addition of 2M NaOH (200 ml) and methanol removed by evaporation. Di-tert-butyldicarbonate (115 g, 0.52 mol) was added followed by 1,4-dioxan (200 ml) and the mixture stirred at room temperature overnight. 1,4-dioxan was removed by evaporation giving a clear oil. To this oil was added 4M HCl in 1,4-dioxan (200 ml) and the mixture stirred at room temperature overnight. The solvent was removed by evaporation to give a white solid (24 g).

1. customby pre-dried
2. filtrationThe mixture was filtered through a pad of celite
3. washthe pad washed with dichloromethane, and solvent
4. customevaporated
5. customto give a clear oil
6. stirringThe mixture was stirred at room temperature overnight
7. customquenched by cautious addition of 2M HCl(aq) (200 ml)
8. additionbasified by addition of 2M NaOH (200 ml) and methanol
9. customremoved by evaporation
10. stirringthe mixture stirred at room temperature overnight
11. custom1,4-dioxan was removed by evaporation
12. customgiving a clear oil
13. stirringthe mixture stirred at room temperature overnight
14. customThe solvent was removed by evaporation

ORD record

ord-3768f328546e48cebc767ac820cdcd66

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576081B2