Methyl iodide → HCID 10803401, compound

To a solution of diisopropylamine (705 μL, 5.03 mmol) in anhydrous THF (12 mL) at −20° was added butyllithium (2.87 mL, 4.60 mmol, 1.6 M in hexane). After the reaction mixture was cooled to −78°, a solution of 4(S)-benzyl-1-(tert-butyldimethyl-silyl)azetidin-2-one (640 mg, 2.32 mmol) in THF (4 mL) was added and the mixture was stirred at −78° for 15 min followed by addition of methyl iodide (488 mg, 214 μL, 3.44 mmol). After 10 min, the reaction mixture was poured into EtOAc (125 mL). The organic phase was washed with aqueous NaHSO4 (1M) and brine, dried (MgSO4), filtered and concentrated. The residual oil was purified by flash chromatography (SiO2, 6% EtOAc in hexane) to give 4(S)-benzyl-1-(tert-butyldimethylsilyl)-3(S)-methylazetidin-2-one (557 mg , 83% yield) as a pale yellow solid. 1H-NMR (400 MHz, CDCl3) δ7.33-7.15 (m, 5H), 3.35 (ddd, J=10.8, 3.8, 2.5 Hz, 1H), 3.21 (dd, J=13.4, 3.8 Hz, 1H), 2.88 (qd, J=7.5, 2.5 Hz, 1H), 2.60 (dd, J=13.4, 10.8 Hz, 1H), 1.02 (d, J=7.5 Hz, 3H), 1.00 (s, 9H), 0.31 (s, 3H), 0.27 (s, 3H).

1. temperatureAfter the reaction mixture was cooled to −78°
2. waitAfter 10 min
3. washThe organic phase was washed with aqueous NaHSO4 (1M) and brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residual oil was purified by flash chromatography (SiO2, 6% EtOAc in hexane)

ORD record

ord-9bb8e3cdbcfe48f7b5db5d2fa245b7d4

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06242439B1