Iodine → 2-Amino-2-isopropylpropane-1,3-diol

Temperature

66 °C

To a solution of 2-amino-2-(hydroxymethyl)-3-methylbutanoic acid (2943 mg, 20 mmol) in THF (60 mL) was added sodium borohydride (2270 mg, 60.0 mmol). The reaction was cooled in an ice bath, and a THF (10 mL) solution of iodine (7614 mg, 30.0 mmol) was added dropwise. The mixture was refluxed (66° C.) for 16 h. The reaction was cooled in an ice bath, and methanol (10 mL) was added (dropwise at first) followed by brine (75 mL). The mixture was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine, dried (MgSO4), then filtered. 4 M HCl in dioxane (6 mL) was added. The mixture was then concentrated. Ether was added, and the precipitate was collected to give the title compound (300 mg) as a white solid.

1. temperatureThe reaction was cooled in an ice bath
2. temperatureThe reaction was cooled in an ice bath
3. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. addition4 M HCl in dioxane (6 mL) was added
8. concentrationThe mixture was then concentrated
9. additionEther was added
10. customthe precipitate was collected

ORD record

ord-609317fef5d84d8db8dd71447c018295

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778950B2