Water → 3-(((2R)-1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethenyl)-1H-indole

HRID 745018Notes

Reaction equation

HRID 745018 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:13]=[CH:14][S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:10][CH:11]=2)[C:6]([CH2:24][C@H:25]2[CH2:29][CH2:28][CH2:27][N:26]2[CH3:30])=[CH:5]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[C:18]1([S:15]([CH:14]=[CH:13][C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][CH:10]=2)[NH:4][CH:5]=[C:6]3[CH2:24][C@H:25]2[CH2:29][CH2:28][CH2:27][N:26]2[CH3:30])(=[O:17])=[O:16])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 54067212(R)-1-acetyl-5-(benzenesulfonylethenyl)-3-(N-methyl-pyrrolidin-2-ylmethyl)-1H-indole

Product 1

HCID 540753983-(((2R)-1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethenyl)-1H-indoleYield 74.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of (R)-1-acetyl-5-(benzenesulfonylethenyl)-3-(N-methyl-pyrrolidin-2-ylmethyl)-1H-indole (220.8 g) in methanol (2.21 L) was treated with potassium carbonate (72.23 g) and stirred at ambient temperature. After about one hour active carbon (22.1 g) was added to the solution then water (660 mL) added slowly. The mixture was filtered and the filtrate heated to reflux and water (660 mL) added dropwise. The mixture was allowed to cool and crystallize, then further water was added slowly (3.31 l). The resulting solid was filtered, washed with 1:2 methanol:water mixture (2×200 mL) then dried in vacuo to give the title compound (149 g): mp, 84°-87° C. IR (KBr) 1600, 1450, 1290, 1145, 1085 cm-1 : 1H NMR (CDCl3) 8.4 (b, 1H), S.0 (d, 2H), 7.8 (d, 1H), 7.7 (s, 1H), 7.6-7.5 (m, 3H), 7.3 (s, 2H), 7.05 (b, 1H), 6.75 (d, 1H), 3.15 (m, 2H), 2.6 (m, 1H), 2.45 (s, 3H), 2.4 (s, 1H), 2.2 (m, 1H), 2.0-.5 (m, 4H); LRMS (TSP), m/z 381, 165, 133, 119.

Workup

  1. additionAfter about one hour active carbon (22.1 g) was added to the solution
  2. filtrationThe mixture was filtered
  3. temperaturethe filtrate heated
  4. temperatureto reflux
  5. additionwater (660 mL) added dropwise
  6. temperatureto cool
  7. customcrystallize
  8. additionfurther water was added slowly (3.31 l)
  9. filtrationThe resulting solid was filtered
  10. washwashed with 1:2 methanol
  11. dry with materialwater mixture (2×200 mL) then dried in vacuo

Sources & evidence

ORD record
ord-a3b996cd4016435595413dd4d1efdf56
Source dataset
uspto-grants-1996_09
Patent number
US05559246

Reaction notes

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