3,4-dihydro-7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methoxy-2(1H)-isoquinolinecarboxylic acid-1,1-dimethylethyl ester → 7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 1078781Notes

Reaction equation

HRID 1078781 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:20][Si](C(C)(C)C)(C)C)=[C:13]([O:18][CH3:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])[CH3:3].[F-].C([NH3+])CCC>O1CCCC1>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:20])=[C:13]([O:18][CH3:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 190420613,4-dihydro-7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methoxy-2(1H)-isoquinolinecarboxylic acid-1,1-dimethylethyl esterHCID 536276511-Butanamine, hydrofluoride

Product 1

HCID 534153467-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 6.0 g portion of 3,4-dihydro-7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-methoxy-2(1H)-isoquinolinecarboxylic acid-1,1-dimethylethyl ester is dissolved in 30 mL tetrahydrofuran and cooled to 0° C. To this is added 22.8 mL of a 1.0M solution of tetra, butylammonium fluoride, while stirring. The reaction mixture is brought to room temperature, and stirred for three hours. The reaction is quenched with 10 mL saturated sodium bicarbonate solution and 10 mL water, followed by the addition of 20 mL diethyl ether. After separating the layers, the aqueous phase is extracted with 2×20 mL diethyl ether. The combined organic layers are washed with 20 mL brine, and dried over magnesium sulfate. Following removal of the solvent, the product is purified by silica gel chromatography (eluting with 2:1 hexane/ethyl acetate) to produce 4.15 g of the desired product as a white solid.

Workup

  1. customis brought to room temperature
  2. stirringstirred for three hours
  3. customThe reaction is quenched with 10 mL saturated sodium bicarbonate solution and 10 mL water
  4. additionfollowed by the addition of 20 mL diethyl ether
  5. customAfter separating the layers
  6. extractionthe aqueous phase is extracted with 2×20 mL diethyl ether
  7. washThe combined organic layers are washed with 20 mL brine
  8. dry with materialdried over magnesium sulfate
  9. customremoval of the solvent
  10. customthe product is purified by silica gel chromatography (eluting with 2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ff57fecce9044b83a1b699f8de12fb7e
Source dataset
uspto-grants-1996_08
Patent number
US05550149

Reaction notes

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