Potassium → (R)-N-Benzyloxymethyl-1-[1-benzyloxymethyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide

HRID 651705Notes

Reaction equation

HRID 651705 reaction equation
[CH2:1]([O:8][CH2:9][N:10]([CH3:42])[S:11]([CH:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:21]=[C:20]2[CH2:35][C@H:36]1[CH2:40][CH2:39][CH2:38][N:37]1[CH3:41])C#N)(=[O:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K]>>[CH2:1]([O:8][CH2:9][N:10]([CH3:42])[S:11]([CH2:14][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:21]=[C:20]2[CH2:35][C@H:36]1[CH2:40][CH2:39][CH2:38][N:37]1[CH3:41])(=[O:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 5462222PotassiumHCID 54237060n-Benzyloxymethyl-1-[(r)-1-benzyloxymethyl-3-(1-methyl-2-pyrrolidinylmethyl)-1h-indol-5-yl]-1-cyano-n-methylmethanesulfonamide

Product 1

HCID 53683333(R)-N-Benzyloxymethyl-1-[1-benzyloxymethyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-N-methylmethanesulfonamideYield 33%

Procedure

To a stirred solution of N-benzyloxymethyl-1-[(R)-1-benzyloxymethyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-1-cyano-N-methylmethanesulfonamide (from step (e), 2.0 g, 3.4 mmol) in IMS (14 ml) at ambient temperature was added 2N potassium hydrodroxide solution (7 ml, 14 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 (3×20 ml). The organic extracts were combined and evaporated in vacuo to yield a dark brown oil. This was purified by flash column chromatography (ethyl acetate:triethylamine 95:5 as eluant) to yield the subtitle compound (631 mg, 33%) as a brown oil.

Workup

  1. temperatureto reflux
  2. temperaturemaintained at this temperature for 15 hr
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. customevaporated in vacuo
  5. customto yield a dark brown oil
  6. customThis was purified by flash column chromatography (ethyl acetate:triethylamine 95:5 as eluant)

Sources & evidence

ORD record
ord-f8c420b3e7b842bab2203d56864b299e
Source dataset
uspto-grants-2001_08
Patent number
US06281357B1

Reaction notes

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