Ethanol → 6-(2-Hydroxy-1,1-dimethyl-ethyl)-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-one

HRID 2069822Notes

Reaction equation

HRID 2069822 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]([CH3:22])([CH3:21])[CH:19]=[O:20])[CH:14]=3)[C:9]2=[O:23])=[CH:5][CH:4]=1.C(O)C.[BH4-].[Na+]>C1COCC1>[OH:20][CH2:19][C:18]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:23])[N:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:25][CH:24]=1)[CH2:17][CH2:16]2)([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 592164762-[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-2-methyl-propionaldehyde

Product 1

HCID 671349876-(2-Hydroxy-1,1-dimethyl-ethyl)-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-oneYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

180 mg 2-[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-2-methyl-propionaldehyde (0.54 mmol, 1 eq) was cooled to zero° C. in 20 ml of a 1:1 mixture of ethanol and THF. 20 mg sodium borohydride (0.54 mmol, 1 eq) was added and the mixture was stirred at 0°° C. for 1 hour. Quenched with water, then 2 drops glacial acetic acid, stirred for 5 minutes, and the mixture concentrated under vacuum to remove the majority of solvents, added saturated bicarb solution, extracted ethyl acetate 2×, dried ethyl acetate over MgSO4, and concentrated to give 180 mg 6-(2-Hydroxy-1,1-dimethyl-ethyl)-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-one (M+H=340) which was used directly in the next reaction with no purification.

Workup

  1. customQuenched with water
  2. stirring2 drops glacial acetic acid, stirred for 5 minutes
  3. concentrationthe mixture concentrated under vacuum
  4. customto remove the majority of solvents
  5. additionadded saturated bicarb solution
  6. extractionextracted ethyl acetate 2×, dried ethyl acetate over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fac19b223faa40019d843aa2ae0e6966
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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