Chlorotrimethylsilane → HCID 15281647, compound

To a stirred suspension of lithium borohydride (0.75 g, 34.4 mmol, 2.0 equiv.) in tetrahydrofuran (60 mL) was added trimethylsilyl chloride (7.48 g, 68.85 mmol, 4.0 equiv.) slowly over a period of 5 minutes at 0° C. under argon. To the reaction mixture was added (S)-2-amino-4,4-dimethyl-pentanoic acid (available from Chem-Impex International, Inc., Wood Dale, Ill., USA; 2.50 g, 17.2 mmol, 1.0 equiv.) in portions over a span of 10 minutes at the same temperature and the reaction was allowed to stir for 24 hours at room temperature. The reaction mixture was quenched with the slow addition of methanol (50 mL) at 0° C., and volatiles were removed by vacuum distillation. The obtained residue was treated with an aqueous solution of 20% potassium hydroxide (w/v; 10 mL) and extracted with dichloromethane (3×20 mL). The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give (S)-2-amino-4,4-dimethyl-pentan-1-ol (1.9 g, 84%).

1. customThe reaction mixture was quenched with the slow addition of methanol (50 mL) at 0° C.
2. customvolatiles were removed by vacuum distillation
3. additionThe obtained residue was treated with an aqueous solution of 20% potassium hydroxide (w/v; 10 mL)
4. extractionextracted with dichloromethane (3×20 mL)
5. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-6d146d8749cf44688b1cadffb4cef64a

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314250B2