Sodium borohydride → N-{2-(4-Hydroxypiperidino)-1-[p-(5-isoquinolinesulfonyloxy)benzyl]ethyl)-N-methyl-5-isoquinolinesulfonamide

HRID 1090569Notes

Reaction equation

HRID 1090569 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([O:14][C:15]3[CH:45]=[CH:44][C:18]([CH2:19][CH:20]([N:29]([CH3:43])[S:30]([C:33]4[C:34]5[CH:35]=[CH:36][N:37]=[CH:38][C:39]=5[CH:40]=[CH:41][CH:42]=4)(=[O:32])=[O:31])[CH2:21][N:22]4[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]4)=[CH:17][CH:16]=3)(=[O:13])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.[BH4-].[Na+]>CO>[OH:28][CH:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH:20]([N:29]([CH3:43])[S:30]([C:33]2[C:34]3[CH:35]=[CH:36][N:37]=[CH:38][C:39]=3[CH:40]=[CH:41][CH:42]=2)(=[O:32])=[O:31])[CH2:19][C:18]2[CH:17]=[CH:16][C:15]([O:14][S:11]([C:6]3[C:5]4[CH:4]=[CH:3][N:2]=[CH:1][C:10]=4[CH:9]=[CH:8][CH:7]=3)(=[O:12])=[O:13])=[CH:45][CH:44]=2)[CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19796283N-{1-[p-(5-Isoquinolinesulfonyloxy)benzyl]-2-(4-oxopiperidino)ethyl)-N-methyl-5-isoquinolinesulfonamide

Product 1

HCID 19796382N-{2-(4-Hydroxypiperidino)-1-[p-(5-isoquinolinesulfonyloxy)benzyl]ethyl)-N-methyl-5-isoquinolinesulfonamideYield 57.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 mg of the amorphous compound obtained in Example 95 was dissolved in 5 ml of methanol, to the solution was added in portions 35.2 mg of sodium borohydride at a room temperature with stirring, and the mixture was stirred for 2 hours and evaporated to remove the solvent. Resulting residue was applied to a silica gel column and eluted with chloroform/methanol (100:4), to obtain 116 mg of the title compound as pale yellow oil.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. customevaporated
  3. customto remove the solvent
  4. washeluted with chloroform/methanol (100:4)

Sources & evidence

ORD record
ord-e75a5e8ec81140f49d74484a55a0ff3a
Source dataset
uspto-grants-1992_01
Patent number
US05081246

Reaction notes

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