Aluminium lithium hydride → (2-Tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropyl)methanol

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Reaction Steps

The solution of ethyl 2-tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropanecarboxylate (12-4) (350 mg, 1.26 mmol) in THF (2 mL) was cooled to 0° C. Then lithium aluminium tetrahydride (72 mg, 1.89 mmol) was added to the solution at 0° C. and it was stirred for 30 min before restored to the room temperature for 1 h. The reaction was quenched in sequence with 0.1 mL water, 0.05 mL 15% NaOH aqueous, 0.1 mL water. The resulting mixture was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by Pre-TLC (PE/EA=1/1). The product was obtained as a white solid (200 mg, 68%). 1H NMR (400 MHz, MeOD) δ 8.24 (s, 1H), 7.55 (dd, J=8.2, 1.7 Hz, 1H), 7.11 (d, J=8.2 Hz, 1H), 3.66-3.58 (m, 3H), 2.33 (s, 3H), 2.13 (t, J=6.6 Hz, 1H), 1.80 (dd, J=6.4, 3.7 Hz, 1H), 1.06 (s, 9H); LRMS (ES) calculated M+H for C14H22NO2: 236.3. Found: 236.2.

Provenance & Evidence