Reaction #1951039

Reaction equation

5,6-Dichloro-2-bromo-3-acetyl-1-[3,5-di-O-(p-toluoyl)-2-deoxy-β-D-ribofuranosyl]indole

sodium methoxide

Water

→

4.143

Yield 68.0%

5,6-Dichloro-2-bromo-3-acetyl-1-(2-deoxy-β-D-ribofuranosyl)indole

Yield 68.0%

Solvents

MeOH

Conditions

Workup

1. 1
   Othera precipitate formed
2. 2
   Otherthe suspension was evaporated until no more MeOH
3. 3
   FiltrationThe remaining solids were filtered
4. 4
   Otherrecrystallized twice from MeOH/H2O

Procedure

5,6-Dichloro-2-bromo-3-acetyl-1-[3,5-di-O-(p-toluoyl)-2-deoxy-β-D-ribofuranosyl]indole (4.142, 1.24 g, 1.7 mmol) was suspended in absolute MeOH (75 mL) to which was added sodium methoxide (250 mg, 4.6 mmol). The suspension was stirred at room temperature for 2 h, after which time the solution first clarified and then a precipitate formed. Water (100 mL) was added, and the suspension was evaporated until no more MeOH remained. The remaining solids were filtered and recrystallized twice from MeOH/H2O to yield 475 mg (68%) of 4.143 as a white crystalline solid: mp slow dec. >235° C.; Rf0.5 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.57 (s, 1H), 8.37 (s, 1H), 6.56 (dd, 1H), 5.46 (s, 1H, D2O exch.), 5.31 (s, 1H, D2O exch.), 4.48 (d, 1H), 3.92 (d, 1H), 3.76 (s, 2H), 2.65 (s, 3H), 2.48 (m, 1H), 2.13 (ddd, 1H). 13C-NMR (125 MHz, DMSO-d6): δ 192.59, 133.20, 126.74, 125.89, 125.77, 121.91, 121.80, 115.94, 115.32, 87.59, 87.30, 69.84, 60.66, 39.23 (under DMSO), 30.95. HRMS (EI) m/z calcd. for C15H14BrCl2NO4 420.9483, found 420.9493. Anal calcd for C15H14BrCl2NO4: C, 42.58; H, 3.34; N, 3.31. Found: C, 42.77; H, 3.25; N, 3.22.

Source