[C:1]([C:3]1([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2].[Li][CH3:16].[BH4-].[Na+].Cl>CO.C1COCC1>[NH2:12][CH:11]([C:10]1[CH:9]=[CH:8][C:7]([C:3]2([C:1]#[N:2])[CH2:6][CH2:5][CH2:4]2)=[CH:14][CH:13]=1)[CH3:16]
4-(Cyanocyclobutyl)benzonitrile (335 mg, 1.84 mmol) is mixed with THF (10.0 mL) and cooled to −78° C. under N2 gas. MeLi (1.15 mL, 1.84 mmol, 1.60M in Et2O) is added, and the mixture is stirred at −78° C. for 15 minutes. A mixture of NaBH4 (70.0 mg, 1.84 mmol) in MeOH (10.0 mL) is added, and the solution is warmed to 0° C. for 1 hour. 1N HCl (40.0 mL) is added, and the solution is concentrated to dryness on the rotovaporator. The product is purified by HPLC: Gilson prep pumps, flow rate: 30 ml/min, column: Synergi Gemini (5u) 21.2×50 mm (high pH), mobile phase: A=water (10 mM NH4CO3) B=MECN, (95.0 mg, 0.475 mmol, 26%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.23 (d, J=6.64 Hz, 3H) 1.90-2.06 (m, 1H) 2.16-2.35 (m, 1H) 2.52-2.64 (m, 2H) 2.64-2.78 (m, 2H) 4.00 (q, J=6.64 Hz, 1H) 7.36 (d, J=8.59 Hz, 2H) 7.42 (d, J=8.20 Hz, 2H).
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