[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH2:20][CH2:19][CH:18]([C:21](OC)=[O:22])[CH2:17][CH:16]=1.CO.[BH4-].[Li+].C(=O)(O)[O-].[Na+]>ClCCl.O>[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:13][CH2:14]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH:16]=1
Methyl 4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]cyclohex-3-ene-1-carboxylate (Example 1, 0.22 g, 0.64 mmol) was dissolved in dichloromethane (10 mL), treated with methanol (0.031 mL, 0.77 mmol, 1.2 equiv) and then lithium borohydride (17 mg, 0.77 mmol, 1.2 equiv). The mixture was stirred at ambient temperature for 30 minutes. To the mixture, eight additional portions of lithium borohydride (17 mg, 0.77 mmol, 1.2 equiv) and eight additional portions of methanol (0.031 mL, 0.77 mmol, 1.2 equiv) were added over 4 hours. The mixture was treated with sodium bicarbonate (20 mL, aqueous saturated), stirred for 18 hours and poured into water (100 mL), which was extracted with ethly acetate (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 7.87 (1H, d, J=8.6 Hz), 7.41 (1H, d, J=8.6 Hz), 5.75-5.72 (1H, m), 4.61 (2H, d, J=7.3 Hz), 3.44-3.37 (1H, m), 3.36-3.32 (1H, m), 2.43-2.33 (1H, m), 2.33-2.23 (2H, m), 1.94-1.85 (2H, m), 1.82-1.74 (1H, m), 1.47-1.34 (2H, m), 0.58-0.53 (2H, m), 0.49-0.45 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 318.1368 [(M+H)+; calculated for C17H21ClN3O: 318.1368].
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