[NH2:1][C:2]1([CH2:7]O)[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.O=S(Cl)Cl.[CH3:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]=[C:25]=[S:26].CN1CCOCC1>ClCCCl>[CH3:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]=[C:25]1[S:26][CH2:7][C:2]2([CH2:6][CH2:5][CH2:4][CH2:3]2)[NH:1]1To a solution of 1-amino-1-(hydroxymethyl)cyclopentane (Method B1c; 20.7 g, 180 mmol) and HCl (4M in p-dioxane, 400 mL) was added SOCl2 (15.7 mL, 216 mmol) and the resulting solution was heated at 100° C. for 18 h. The reaction mixture was concentrated under reduced pressure, then treated with 2-methyl4-nitrophenyl isothiocyanate (31.4 g, 162 mmol) and 1,2-dichloroethane (400 ml), followed by N-methylmorpholine (49 mL, 449 mmol). The resulting mixture was heated at 70° C. for 18 h, cooled to room temp. and concentrated under reduced pressure. The residue was treated with hot EtOAc, filtered and concentrated under reduced pressure. The residue was recrystallized (MeOH) to yield 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane (38.3 g, 81%): TLC (25% EtOAc/hex) Rf0.27.
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