Water → 2-(3-Bromo-2-hydroxymethyl-phenyl)-6-(1-hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-one

HRID 589512Notes

Reaction equation

HRID 589512 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]([OH:23])([CH3:22])[CH3:21])[CH:16]=3)[C:11]2=[O:24])[C:3]=1[CH:4]=[O:5].C([BH-](CC)CC)C.[Li+].C([O-])(O)=O.[Na+].O>C1COCC1>[Br:1][C:2]1[C:3]([CH2:4][OH:5])=[C:6]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]([OH:23])([CH3:21])[CH3:22])[CH:16]=3)[C:11]2=[O:24])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 23664628LithiumtriethylborohydrideHCID 867310022-Bromo-6-[6-(1-hydroxy-1-methyl-ethyl)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-benzaldehyde

Product 1

HCID 712310502-(3-Bromo-2-hydroxymethyl-phenyl)-6-(1-hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 42 (320 mg, 0.824 mmol) in THF (10 ml) under argon atmosphere was added lithium triethylborohydride (1M in THF, 0.989 ml, 0.989 mmol) dropwise. The resulting mixture was stirred for 2 hrs at r.t. before adding sat. aqueous NaHCO3 solution (5 ml). Additional water was added and the mixture was extracted three times with EtOAc. The combined organic layers were dried, filtered, and evaporated to dryness. The crude product was purified by flash chromatography (silica gel, cyclohexane/EtOAC gradient) to yield Intermediate 43.

Workup

  1. extractionthe mixture was extracted three times with EtOAc
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified by flash chromatography (silica gel, cyclohexane/EtOAC gradient)

Sources & evidence

ORD record
ord-c2600f28670f415c8301abc3d3ada72d
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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