[CH:1]1([C@H:4]([NH2:6])[CH3:5])[CH2:3][CH2:2]1.C([O:9][C:10]([C:12]1[N:13]([CH2:25][CH2:26]Br)[N:14]=[C:15]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=1)=O)C.[I-].[K+]>C(#N)C>[CH:1]1([C@H:4]([N:6]2[CH2:26][CH2:25][N:13]3[N:14]=[C:15]([CH2:17][O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:16]=[C:12]3[C:10]2=[O:9])[CH3:5])[CH2:3][CH2:2]1(R)-1-Cyclopropylethylamine (0.3 mL, 2.82 mmol) was added to a suspension of 2-(2-bromo-ethyl)-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (100 mg, 0.128 mmol) and potassium iodide (9.36 mg, 0.056 mmol) in ACN (1 mL). The mixture was stirred at 90° C. for 20 hours. The solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80). The desired fractions were collected and the solvents evaporated in vacuo to yield (R)-5-(1-cyclopropyl-ethyl)-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one as a orange oil. 1H NMR (500 MHz, CDCl3) δ ppm 0.29-0.37 (m, 1H), 0.38-0.49 (m, 2H), 0.60-0.70 (m, 1H), 0.86-0.97 (m, 1H), 1.28 (d, J=6.9 Hz, 3H), 3.75 (ddd, J=12.9, 7.6, 4.9 Hz, 1H), 3.87 (ddd, J=12.9, 7.4, 5.2 Hz, 1H), 4.07 (dq, J=9.2, 6.9 Hz, 1H), 4.32-4.44 (m, 2H), 5.09 (s, 2H), 6.92 (s, 1H), 6.96 (t, J=7.4 Hz, 1H), 6.98-7.03 (m, 2H), 7.27-7.32 (m, 2H).
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