Potassium Hydroxide → (r)-n-Benzyl-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1h-indol-5-yl]-n-methylmethanesulfonamide

HRID 651696Notes

Reaction equation

HRID 651696 reaction equation
[CH2:1]([N:8]([CH3:38])[S:9]([CH:12]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:19]=[C:18]2[CH2:31][C@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[CH3:37])C#N)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([N:8]([CH3:38])[S:9]([CH2:12][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH:19]=[C:18]2[CH2:31][C@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[CH3:37])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59966110N-Benzyl-1-[(R)-1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-1-cyano-N-methylmethanesulfonamide

Product 1

HCID 53689728(r)-n-Benzyl-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1h-indol-5-yl]-n-methylmethanesulfonamideYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of N-benzyl-1-[(R)-1-benzyl-3-(1-methyl-2-pyrrolidinylethyl)-1H-indol-5-yl]-1-cyano-N-methylmethanesulfonamide (from step (e), 29 g, 55.1 mmol) in ethanol (200 ml) at ambient temperature was added 2N potassium hydroxide solution (200 ml, 400 mmol). The dark brown solution was then brought to reflux and maintained at this temperature for 15 hr. The oily reaction mixture was then cooled to ambient temperature and extracted with ethyl acetate (3×300 ml). The organic extracts where combined and evaporated in vacuo to give a dark brown oil. This was purified by flash column chromatography (ethyl acetate:hexane:diethylamine 1:1:0.1 as eluant) to yield the subtitle compound (24.67 g, 89%) as a brown oil.

Workup

  1. temperatureto reflux
  2. temperaturemaintained at this temperature for 15 hr
  3. extractionextracted with ethyl acetate (3×300 ml)
  4. customevaporated in vacuo
  5. customto give a dark brown oil
  6. customThis was purified by flash column chromatography (ethyl acetate:hexane:diethylamine 1:1:0.1 as eluant)

Sources & evidence

ORD record
ord-2254eabbd0054d118596728c74e69362
Source dataset
uspto-grants-2001_08
Patent number
US06281357B1

Reaction notes

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