Ammonium Acetate → 1-(5-Isoquinolinesulfonyl)-3-amino-5-methylpyrrolidine

HRID 2291950Notes

Reaction equation

HRID 2291950 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([N:14]3[CH:18]([CH3:19])[CH2:17][C:16](=O)[CH2:15]3)(=[O:13])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+]>CO>[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([N:14]3[CH:18]([CH3:19])[CH2:17][CH:16]([NH2:27])[CH2:15]3)(=[O:13])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 143268571-(5-Isoquinolinesulfonyl)-5-methyl-3-pyrrolidone

Product 1

HCID 143268581-(5-Isoquinolinesulfonyl)-3-amino-5-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To 30 ml of methanol were added 1.45 g of the thus obtained 1-(5-isoquinolinesulfonyl)-5-methyl-3-pyrrolidone, 0.39 g of ammonium acetate and 0.32 g of sodium cyanoborohydride, followed by stirring at 20° C. for 24 hours. The methanol was removed under reduced pressure, and 100 ml of chloroform was added to the resultant product. Then, the mixture was washed twice with 50 ml each of water, washed once with 50 ml of a 50% aqueous sodium hydrogencarbonate solution, and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a residue. The residue thus obtained was subjected to purification by silica gel column chromatography (Wacogel C200, 50 g; solvent: chloroform) to obtain 0.96 g of 1-(5-isoquinolinesulfonyl)-3-amino-5-methylpyrrolidine [Compound (77)]. Compound (77) was analyzed to give the following data.

Workup

  1. customThe methanol was removed under reduced pressure, and 100 ml of chloroform
  2. additionwas added to the resultant product
  3. washThen, the mixture was washed twice with 50 ml each of water
  4. washwashed once with 50 ml of a 50% aqueous sodium hydrogencarbonate solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto obtain a residue
  8. customThe residue thus obtained
  9. customwas subjected to purification by silica gel column chromatography (Wacogel C200, 50 g; solvent: chloroform)

Sources & evidence

ORD record
ord-dd81f3dd37d142b6864e04860a94257f
Source dataset
uspto-grants-1989_01
Patent number
US04798897

Reaction notes

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