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0 °C

A solution of nitrile 26C (1.1 g, 3.3 mmol) in diethyl ether (30 mL) was added in small amounts to a mixture of LiAlH4 (0.25 g, 2 mol eq) in diethyl ether (30 mL) stirred at 0° C. After the addition was completed, the mixture was stirred at room temperature overnight. The excess of LiAlH4 was destroyed at 0° C. by addition of small amount of water (30 mL), the solid formed was filtered off and the organic filtrate was separated, washed with brine (50 mL) and dried over Na2SO4. The organic phase was evaporated under reduced pressure and the residue was purified by flash chromatography (7:3 EtOAc:MeOH) to afford 27C as a pale yellow oil (0.87 g, 77% yield). 1HNMR (DMSO, 400 MHz) δ 1.97 (m, 4H), 3.48 (m, 4H), 3.68 (s, 2H), 4.15 (bs, 2H), 6.44 (s, 1H), 7.15 (s, 1H), 7.43 (d, 2H, J=8), 8.17 (d, 2H, J=8).

1. additionAfter the addition
2. stirringthe mixture was stirred at room temperature overnight
3. customThe excess of LiAlH4 was destroyed at 0° C. by addition of small amount of water (30 mL)
4. customthe solid formed
5. filtrationwas filtered off
6. customthe organic filtrate was separated
7. washwashed with brine (50 mL)
8. dry with materialdried over Na2SO4
9. customThe organic phase was evaporated under reduced pressure
10. customthe residue was purified by flash chromatography (7:3 EtOAc:MeOH)