[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]2)=[C:4]([CH3:20])[CH:3]=1.[C:21](O)(=O)C.C=O.O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:21])[CH:9]2[CH2:10][N:11]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:12]2)=[C:4]([CH3:20])[CH:3]=1A solution of tert-butyl 3-((4-fluoro-2-methylphenyl)amino)azetidine-1-carboxylate (D30) (240 mg, 0.856 mmol), acetic acid (0.49 ml, 8.56 mmol), Formaldehyde 36% wt. in water (0.066 ml, 0.856 mmol) and sodium(triacetoxy)borohydride (725 mg, 3.424 mmol) in 1,2-dichloroethane (7 ml) was stirred under N2 atmosphere at room temperature for 1 day. NaHCO3 sat. solution (25 ml) was added. After phase separation, the aqueous layer was extracted with dichloromethane (2×35 ml). The organics after solvent evaporation were purified by Biotage SNAP-Si cartridge (10 g) eluting with cyclohexane/ethylacetate from 90/10 up to 80/20. Collected fractions after solvent evaporation afforded the title compound (D33) (170 mg)
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