[CH2:1]([O:8][C:9](=[O:21])[NH:10][CH:11]1[CH2:18][CH2:17][CH:16]2[CH2:19][CH:12]1[CH2:13][CH2:14][C:15]2=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:21])[NH:10][CH:11]1[CH2:18][CH2:17][CH:16]2[CH2:19][CH:12]1[CH2:13][CH2:14][CH:15]2[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1780 mg of (6-Oxo-bicyclo[3.3.1]non-2-yl)-carbamic acid benzyl ester (100) were dissolved in 14 mL of THF under argon, cooled to 0° C. and 113 mg of sodium borohydride were added. The mixture was stirred for 2 h at 0° C., water was added and the pH of solution was adjusted to 2 by addition of 2M HCl. The aqueous layer was extracted with ethyl acetate three times. The combined organic layer was dried over sodium sulfate and evaporated to dryness to give 0.72 g of the desired product. Rt=1.23 min (Method C). Detected mass: 290.3 (M+H+).
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