Potassium Hydroxide → HCID 54331189, compound

HRID 651707Notes

Reaction equation

HRID 651707 reaction equation
[CH2:1]([N:8]([CH3:39])[S:9]([CH:12](C#N)[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][O:23][C@H:24]([Si:26]([CH3:29])([CH3:28])[CH3:27])[CH3:25])[CH:17]=[C:16]2[CH2:30][CH:31]1[CH2:35][CH2:34][CH2:33][N:32]1[CH3:36])(=[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]([CH3:39])[S:9]([CH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][O:23][C@H:24]([Si:26]([CH3:27])([CH3:28])[CH3:29])[CH3:25])[CH:17]=[C:16]2[CH2:30][CH:31]1[CH2:35][CH2:34][CH2:33][N:32]1[CH3:36])(=[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 70104646HCID 70104646, compound

Product 1

HCID 54331189HCID 54331189, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of N-benzyl-1-cyano-N-methyl-1-[(R)-3-(1-methyl-2-pyrrolidinylmethyl)-1-trimethylsilylethyloxymethyl-1H-indol-5-yl]methanesulfonamide (from step (b), 1.56 g, 2.8 mmol) in ethanol (12 ml) at ambient temperature was added 2N potassium hydroxide solution (6.24 ml, 12.5 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 (3×25 ml). The organic extracts were combined and evaporated in vacuo to yield the crude product as a dark brown oil. This was purified by flash column chromatography (ethyl acetate:hexane:dietiylamine 1:1:0.1 as eluant) to yield the title compound (1.49 g, 75%) as a brown oil.

Workup

  1. temperatureto reflux
  2. temperaturemaintained at this temperature for 15 hr
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. customevaporated in vacuo
  5. customto yield the crude product as a dark brown oil
  6. customThis was purified by flash column chromatography (ethyl acetate:hexane:dietiylamine 1:1:0.1 as eluant)

Sources & evidence

ORD record
ord-517df6a4524945a0a89e03ee62eca504
Source dataset
uspto-grants-2001_08
Patent number
US06281357B1

Reaction notes

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