Boron trichloride methyl sulfide → (3aR,4R,5R,6R,7aS)-2-(azetidin-1-yl)-6-(hydroxymethyl)-3a,4,5,6,7,7a-hexahydrobenzo[d]thiazole-4,5-diol
Reaktionsgleichung
B(Cl)(Cl)Cl.CSC.[N:8]1([C:12]2[S:13][C@H:14]3[CH2:20][C@H:19]([CH2:21][O:22]CC4C=CC=CC=4)[C@@H:18]([O:30]CC4C=CC=CC=4)[C@H:17]([O:38]CC4C=CC=CC=4)[C@H:15]3[N:16]=2)[CH2:11][CH2:10][CH2:9]1>>[N:8]1([C:12]2[S:13][C@H:14]3[CH2:20][C@H:19]([CH2:21][OH:22])[C@@H:18]([OH:30])[C@H:17]([OH:38])[C@H:15]3[N:16]=2)[CH2:11][CH2:10][CH2:9]1Komponenten
3
Edukt 2
Produkt 1
Versuchsvorschrift
This compound was prepared by boron trichloride-methyl sulfide de-benzylation via a procedure as described above in Example 4, Step 3 from (3aR,4R,5R,6R,7aS)-2-(Azetidin-1-yl)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3a,4,5,6,7,7a-hexahydrobenzo[d]thiazole (0.220 g, 0.417 mmol). Purification on silica gel by flash column chromatography (1.0 M NH3 in MeOH/CH2Cl2, 1:4), afforded the title compound as an off-white solid (0.052 g, 48%). 1H NMR (400 MHz, CD3OD) δ 4.37-4.33 (m, 1H), 4.08-3.98 (m, 4H), 3.80-3.75 (m, 2H), 3.62 (dd, J=6.3, 10.8 Hz, 1H), 3.40 (t, J=9.1, 1H), 3.32 (t, J=9.8 Hz, 1H), 2.35 (quint, J=7.6, 2H), 2.22-2.17 (m, 1H), 1.96-1.89 (m, 1H), 1.78-1.70 (m, 1H); 13C NMR (100 MHz, CD3OD) δ 167.63, 78.24, 76.76, 74.30, 64.03, 55.10, 53.30, 40.73, 26.99, 17.58; MS, m/z=281 (M+23).