[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].OS([O-])(=O)=O.[Na+]>C(Cl)Cl.O>[Cl:1][C:2]1[C:3]([CH2:4][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:6][CH:7]=[CH:8][C:9]=1[OH:10]
2-Chloro-3-hydroxybenzaldehyde (4.5 g, 0.03 mol) was added in portions for 30 min to a mixture of pyrrolidine (3. mL, 0.036 mol) and NaB(OAc)3H (7.6 g, 0.036 mol) in CH2Cl2 (50 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon. The mixture was stirred for 3 h and cooled with an ice bath. Water (50 mL) and 5N NaHSO4 (to pH 1) were added. The organic layer was separated and discarded. The aqueous one was alkalized with saturated K2CO3 to pH 6 and extracted with chloroform (2×50 mL). The combined extracts were dried with Na2SO4, and evaporated to give the title compound (5.76 g, 95%) as white crystals. LCMS-data: (M+H)+ 214.0 and 212.0 (calculated for C11H14ClNO 211.7). 1H NMR data (DMSO-d6): 9.95 (br. s, 1H, ArOH), 7.07 (t, 1H, J1=7.8 Hz, J2=15.7, Ar—H), 6.90 (dd, 1H, J1=1.5 Hz, J2=7.6 Hz, Ar—H); 6.85 (dd, 1H, J1=1.5, J2=9.5, Ar—H), 3.63 (s, 2H, ArCH2), 2.43-2.50 (m, 4H, pyrrolidine (CH2)2N), 1.63-1.73 (m, 4H, CH2CH2CH2CH2).
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