Boron trichloride methyl sulfide → (3aR,4R,5R,6R,7aS)-2-(dimethylamino)-6-(hydroxymethyl)-3a,4,5,6,7,7a-hexahydrobenzo[d]thiazole-4,5-diol

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Reaction Steps

Prepared by boron trichloride-methyl sulfide de-benzylation via a procedure as described above in Intermediate Example 4 Step 3 from (3aR,4R,5R,6R,7aS)-2-(dimethylamino)-4,5-bisbenzyloxy-6-(benzyloxyoxymethyl)-3a,4,5,6,7,7a-hexahydrobenzo[d]thiazole (0.270 g, 0.523 mmol). Purification on silica gel by flash column chromatography (1.0 M NH3 in MeOH/CH2Cl2, 1:4), afforded the product as an off-white solid (0.048 g, 36%). 1H NMR (400 MHz, CD3OD) δ 4.36-4.33 (m, 1H), 3.81-3.76 (m, 2H), 3.63 (dd, J=6.3, 10.8 Hz, 1H), 3.41 (t, J=9.1 Hz, 1H), 3.31 (t, J=9.8 Hz, 1H), 3.02 (s, 6H), 2.24-2.19 (m, 1H), 1.97-1.93 (m, 1H), 1.79-1.71 (m, 1H); 13C NMR (100 MHz, CD3OD) δ 171.90, 77.01, 73.49, 70.83, 63.54, 52.60, 41.98, 40.84, 26.53; MS, m/z=269 (M+23).

Provenance & Evidence