Sodium Bicarbonate → 3-[2-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-4-(hydroxymethyl)-1-oxo-1,2-dihydroisoquinolin-6-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamide

HRID 906424Notes

Reaction equation

HRID 906424 reaction equation
[BH4-].[Na+].[Si:3]([O:10][CH2:11][C:12]([CH3:42])([CH3:41])[CH2:13][N:14]1[CH:23]=[C:22]([CH:24]=[O:25])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:26]3[CH:27]=[C:28]([CH:35]=[C:36]([F:39])[C:37]=3[CH3:38])[C:29]([NH:31][CH:32]3[CH2:34][CH2:33]3)=[O:30])[CH:20]=2)[C:15]1=[O:40])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].C([O-])(O)=O.[Na+]>C(O)C>[Si:3]([O:10][CH2:11][C:12]([CH3:42])([CH3:41])[CH2:13][N:14]1[CH:23]=[C:22]([CH2:24][OH:25])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:26]3[CH:27]=[C:28]([CH:35]=[C:36]([F:39])[C:37]=3[CH3:38])[C:29]([NH:31][CH:32]3[CH2:33][CH2:34]3)=[O:30])[CH:20]=2)[C:15]1=[O:40])([C:6]([CH3:8])([CH3:9])[CH3:7])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 866409693-[2-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamide

Product 1

HCID 673911003-[2-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-4-(hydroxymethyl)-1-oxo-1,2-dihydroisoquinolin-6-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.804 g) was added to a stirred solution of 3-[2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamide (Example 26f, 8 g) in ethanol (80 mL) at room temperature under nitrogen. After 5 min, saturated aqueous NaHCO3 (40 mL) was added and the mixture extracted with ethyl acetate (100 mL). The organic layer was washed with water (40 mL), dried (Na2SO4), filtered and evaporated. The residue was purified (SiO2 chromatography, elution with 5-50% ethyl acetate in isohexane) to give the subtitle compound (5.72 g) as a solid.

Workup

  1. extractionthe mixture extracted with ethyl acetate (100 mL)
  2. washThe organic layer was washed with water (40 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified
  7. wash(SiO2 chromatography, elution with 5-50% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-61bf2542ef194df095a252d6d3185dae
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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