[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Si:6]([O:13][C:14]1[C:15]([F:22])=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl>[Si:6]([O:13][C:14]1[C:15]([F:22])=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]
Pyrrolidine (6.8 mL, 82 mmol) was added to a solution of intermediate 32, 3-{[tert-butyl(dimethyl)silyl]oxy}-2-fluorobenzaldehyde (16.7 g, 66 mmol) in dichloromethane (200 mL). The reaction mixture was cooled on ice bath, and sodium triacetoxyborohydride (17.4 g, 82 mmol) was added in portions under stirring. The reaction mixture was intensively stirred for 12 h at RT. Water (100 mL) was added. The organic layer was separated. The aqueous one was extracted with CH2Cl2 (2×100 mL). The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo to give the title compound (19 g, 94%, 60 mmol). 1H NMR data (DMSO-d6): 6.92-7.03 (m, 2H, H—Ar), 6.83-6.91 (m, 1H, H—Ar), 3.58 (d, 2H, J=1.7 Hz, Ar—CH2); 2.38-2.46 (m, 4H), 1.63-1.70 (m, 4H) 0.97 (s, 9H, t-Bu), 0.16 (s, 6H, 2CH3).
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