Potassium Hydroxide → (R)-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-N-diphenylmethyl-N-methylmethanesulfonamide

HRID 651701Notes

Reaction equation

HRID 651701 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17](C#N)[S:18]([N:21]([CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:22])(=[O:20])=[O:19])=[CH:14][CH:15]=2)[C:10]([CH2:38][C@H:39]2[CH2:43][CH2:42][CH2:41][N:40]2[CH3:44])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][S:18]([N:21]([CH:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH3:22])(=[O:19])=[O:20])=[CH:14][CH:15]=2)[C:10]([CH2:38][C@H:39]2[CH2:43][CH2:42][CH2:41][N:40]2[CH3:44])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 540937701-[(R)-1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-1-cyano-N-diphenylmethyl-N-methylmethanesulfonamide

Product 1

HCID 57119402(R)-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-N-diphenylmethyl-N-methylmethanesulfonamideYield 61.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 1-[(R)-1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-1-cyano-N-diphenylmethyl-N-methylmethanesulfonamide (from step (d), 11.61 g, 19.3 mmol) in ethanol (35 ml) at ambient temperature was added 2N potassium hydroxide solution (35 ml, 70 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 (3×100 ml). The organic extracts were combined and evaporated in vacuo to yield the crude product as a dark brown oil. The oil was diluted with ethanol (35 ml) and stirred at ambient temperature for 12 hr, which resulted in precipitation. The mixture was then filtered and the solid dried in vacuo at 50° C. overnight to yield the title compound (6.82 g, 61%) as a beige solid. m.p. 117-120° C.

Workup

  1. temperatureto reflux
  2. temperaturemaintained at this temperature for 15 hr
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. customevaporated in vacuo
  5. customto yield the crude product as a dark brown oil
  6. customwhich resulted in precipitation
  7. filtrationThe mixture was then filtered
  8. customthe solid dried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-3185ec7fc159400bbd32c45ca89e96cb
Source dataset
uspto-grants-2001_08
Patent number
US06281357B1

Reaction notes

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