Sodium Hydroxide → tert-Butyl (2S)-4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)methyl]-2-methylpiperazine-1-carboxylate

HRID 906435Notes

Reaction equation

HRID 906435 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7](S(C1C=CC=CC=1)(=O)=O)[CH:6]=[C:5]2[CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@@H:25]([CH3:36])[CH2:24]1.[OH-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[C:5]2[CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@@H:25]([CH3:36])[CH2:24]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67130295tert-Butyl (2S)-4-{[6-bromo-1-oxo-2-(phenylsulfonyl)-1,2-dihydroisoquinolin-4-yl]methyl}-2-methylpiperazine-1-carboxylate

Product 1

HCID 67438201tert-Butyl (2S)-4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)methyl]-2-methylpiperazine-1-carboxylateYield 32.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of tert-butyl (2S)-4-{[6-bromo-1-oxo-2-(phenylsulfonyl)-1,2-dihydroisoquinolin-4-yl]methyl}-2-methylpiperazine-1-carboxylate (Example 34a, 3.2 g) dissolved in DMF (20 mL) was treated with sodium hydroxide (0.444 g) in water (20 mL) under nitrogen. The resulting mixture was stirred at 20° C. for 2 h. The reaction mixture was diluted with water (20 mL), and extracted with ethyl acetate (25 mL). The organics were dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified (SiO2 chromatography, elution 100% diethyl ether). Pure fractions were evaporated to dryness to afford the subtitle compound (0.780 g) as a solid.

Workup

  1. extractionextracted with ethyl acetate (25 mL)
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified
  7. wash(SiO2 chromatography, elution 100% diethyl ether)
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-bc47b4541abf491a9dc08a6b5a59e945
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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