Chlorotrimethylsilane → 2-Amino-4,4,4-trifluorobutan-1-ol

To a suspension of LiBH4 (62.7 mg, 2.88 mmol) in THF (1.5 mL) was added TMSCl (728 μL, 5.76 mmol) and the reaction mixture was stirred at room temperature for 15 min, followed by the addition of 2-amino-4,4,4-trifluorobutanoic acid (226 mg, 1.44 mmol). The reaction mixture was stirred at room temperature for 18 h, and quenched by careful addition of MeOH. The solvents were removed by reduced pressure, and to the residue was added H2O (2.08 mL). The resulting aqueous portion was made basic by adding 2 N NaOH. The mixture was extracted with CH2Cl2 three times. The combined organic portions were dried over MgSO4, filtered and concentrated to give 2-amino-4,4,4-trifluorobutan-1-ol as a colorless oil (110 mg, 53% yield). NMR: 400 MHz 1H (CDCl3) 3.61 ppm, 1 H, dd, J=10.61, 4.04 Hz; 3.42 ppm, 1 H, m; 3.28 ppm, 1 H, m; 2.29 ppm, 1 H, m; 2.12 ppm, 1 H, m.

1. stirringThe reaction mixture was stirred at room temperature for 18 h
2. customquenched by careful addition of MeOH
3. customThe solvents were removed by reduced pressure
4. additionto the residue was added H2O (2.08 mL)
5. additionby adding 2 N NaOH
6. extractionThe mixture was extracted with CH2Cl2 three times
7. dry with materialThe combined organic portions were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-401086c64e2c4d21b2e5e4d4ece259c1

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888376B2