[CH2:1]1[CH:10]2[C:4](=[N:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9]2=[O:11])[CH2:3][CH2:2]1.C([BH3-])#N.[Na+].Cl.CO.C(=O)([O-])O.[Na+]>CO.O1CCCC1.CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.O>[CH2:1]1[CH:10]2[CH:4]([NH:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9]2=[O:11])[CH2:3][CH2:2]1
2,3,9,10a-Tetrahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one (38.3 g, 0.19 mmol) and bromocresol green (30 mg) were suspended in a mixture of methanol (200 mL) and tetrahydrofuran (200 mL), which was cooled to 0° C. To the suspension was added, at the same temperature, sodium cyanoborohydride (13.2 g, 0.21 mmol), to which was then added dropwise gradually a 10% hydrogen chloride-methanol solution until no more color change of the reaction system was observed. To the reaction mixture was added water (500 mL), which was made alkaline with a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform three times. Organic layers were combined, washed with water and a saturated aqueous solution of sodium chloride, dried over sodium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure to give 38.5 g (yield 99%) of the titled compound. The sample for analytical use was prepared by recrystallization from ethanol as a cis-trans mixture (1:1). m.p. 191°-212° C.
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