[BH4-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]3[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.C(Cl)Cl>CO.O1CCCC1>[O:6]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]3[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[O:3][CH2:4][CH2:5]1Sodium borohydride (3.78 g, 100 mmol) was added in four portions to a stirred solution of 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzaldehyde (4.94 g, 20 mmol) (Taylor, E. C., Skotnicki, J. S. Synthesis, 1981, 606) in methanol/tetrahydrofuran (1:1, 100 mL) at 0° C. and the resulting solution was stirred at 0° C. for 30 minutes and then at room temperature for 1 hour. Methylene chloride was added and the solution was washed with water and dried over sodium sulfate. The solvents were removed and the residue was solidified upon standing (5.0 g, 100%); 1H NMR (300 MHz, CDCl3) δ 1.84 (t, J=5.7 Hz, 4H), 3.33 (t, J=5.7 Hz, 4H), 3.99 (s, 4H), 4.59 (d, J=5.8 Hz, 2H), 6.93 (d, J=8.7 Hz, 2H), 7.24 (d, J=8.7 Hz, 2H); MS (ES) m/z: 249.9 (MH+); HRMS Calcd. for C14H20NO3 (MH+): 250.1443. Found: 250.1434.
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