Sodium Hydroxide → HCID 44594458, compound

HRID 1694577Notes

Reaction equation

HRID 1694577 reaction equation
C(O)(=O)CCC(O)=O.[C:9](=[O:12])([OH:11])[OH:10].[NH:13]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19]2[C:20]3[CH:21]=[CH:22][N:23]=[CH:24][C:25]=3[CH:26]=[CH:27][CH:28]=2)[CH2:14]1.[OH-].[Na+]>C(OC(C)C)(=O)C>[C:9](=[O:10])([OH:12])[OH:11].[NH:13]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19]2[C:20]3[CH:21]=[CH:22][N:23]=[CH:24][C:25]=3[CH:26]=[CH:27][CH:28]=2)[CH2:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67280770HCID 67280770, compound

Product 1

HCID 44594458HCID 44594458, compound

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

(R)-N-(pyrrolidin-3-yl)isoquinolin-5-amine carbonate succinic acid salt (3.0 g, 9.06 mmol, from Example 5) was slurried in 100 mL of isopropyl acetate. To the slurry was added 0.5 N NaOH (50 mL) and the biphasic mixture was stirred until all solids dissolved. The aqueous layer was separated and the organic layer was washed with 50 mL of water. CO2 gas was bubbled through the wet isopropyl acetate solution with stirring. The solution became light yellow and a solid began to form. After 5 minutes, the CO2 source was removed and the slurry was stirred for 2 hours. The suspension was filtered and washed with 10 mL of isopropyl acetate. (R)-N-(pyrrolidin-3-yl)isoquinolin-5-amine carbonic acid salt was isolated as a solid (1.2 g).

Workup

  1. dissolutiondissolved
  2. customThe aqueous layer was separated
  3. washthe organic layer was washed with 50 mL of water
  4. customCO2 gas was bubbled through the wet isopropyl acetate solution
  5. stirringwith stirring
  6. customto form
  7. customthe CO2 source was removed
  8. stirringthe slurry was stirred for 2 hours
  9. filtrationThe suspension was filtered
  10. washwashed with 10 mL of isopropyl acetate

Sources & evidence

ORD record
ord-319c20978ccc4b4b92a4716b80244d11
Source dataset
uspto-grants-2012_04
Patent number
US08158796B2

Reaction notes

Loading…