Water → HCID 21100538, compound

HRID 1352458Notes

Reaction equation

HRID 1352458 reaction equation
C([C@H]([C@@H](C(O)=O)O)O)(O)=O.[CH2:11]([N:18]1[CH2:22][CH2:21][CH:20]([C:23]2[NH:24][C:25](=[O:34])[C:26]3[C:31]([CH:32]=2)=[C:30]([CH3:33])[CH:29]=[CH:28][CH:27]=3)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)Cl.[OH-].[Na+].O>CO>[CH2:11]([N:18]1[CH2:22][CH2:21][CH:20]([C:23]2[NH:24][C:25](=[O:34])[C:26]3[C:31]([CH:32]=2)=[C:30]([CH3:33])[CH:29]=[CH:28][CH:27]=3)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 21100537HCID 21100537, compound

Product 1

HCID 21100538HCID 21100538, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Subsequently, the crystals recovered from the mother liquor of the recrystallization was recrystallized three times from methanol to yield (11.74 g). (−)-3-(1-Benzylpyrrolidin-3-yl)-5-methyl-2H-isoquinolin-1-one D-tartrate (38.8 g) was stirred in methanol (150 ml)-methylene chloride (300 ml), 1N aqueous sodium hydroxide solution (200 ml) and water (100 ml) were added dropwise to alkalify the solution. The methylene chloride layer was partitioned and washed with water, and then dried over magnesium sulfate and concentrated to give (−)-3-(1-benzylpyrrolidin-3-yl)-5-methyl-2H-isoquinolin-1-one (27.5 g).

Workup

  1. customSubsequently, the crystals recovered from the mother liquor of the recrystallization
  2. customwas recrystallized three times from methanol
  3. customto yield (11.74 g)
  4. additionwere added dropwise
  5. customThe methylene chloride layer was partitioned
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6ace6f78dff8480282fd448d03f7410d
Source dataset
uspto-grants-2007_05
Patent number
US07220759B2

Reaction notes

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