Methanol → HCID 86594486, compound

Temperature

25 °C

To a stirring solution of lithium borohydride (14.5 mL of a 2M solution in THF, 29 mmol) at 0° C. was added chlorotrimethylsilane (7.38 mL, 58 mmol) dropwise over a period of 30 min. The ice bath was removed and the resulting slurry was stirred at 25° C. for 30 min. The reaction mixture was cooled to 0° C. and 5,5,5-trifluoro-L-alloisoleucine (2.7 g, 16.98 mmol) was added in portions as a solid over a period of 15 min. The reaction mixture was allowed to warm slowly to 25° C. as the ice bath melted. After 3 days at 25° C., the reaction mixture was cooled to 0° C., and methanol (22 mL) was carefully added over a period of 30 min. The solution was stirred at 25° C. for an additional 40 min, then concentrated under reduced pressure in a water bath at 60° C. The resulting slurry was made basic with 20% sodium hydroxide (10 mL). Water (10 mL) was added, and the entire aqueous layer was extracted with methylene chloride (100 mL) and dried over MgSO4. The organic phase was filtered and evaporated to produce (2S,3R)-2-amino-5,5,5-trifluoro-3-methylpentan-1-ol as a crude oil (2.6 g, 89.6%). Mass Spectrum (−ESI): 170 (M−H)−.

1. customThe ice bath was removed
2. temperatureThe reaction mixture was cooled to 0° C.
3. waitAfter 3 days at 25° C.
4. temperaturethe reaction mixture was cooled to 0° C.
5. stirringThe solution was stirred at 25° C. for an additional 40 min
6. concentrationconcentrated under reduced pressure in a water bath at 60° C
7. additionWater (10 mL) was added
8. extractionthe entire aqueous layer was extracted with methylene chloride (100 mL)
9. dry with materialdried over MgSO4
10. filtrationThe organic phase was filtered
11. customevaporated

ORD record

ord-0dc6eb119c5247a2ae261b8bb3a97341

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858658B2