Water → 2-(tert-Butoxycarbonyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 565396Notes

Reaction equation

HRID 565396 reaction equation
O.CC(C)([O-])C.[K+].C[O:9][C:10]([CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][C:17]([O:24][CH3:25])=[C:18]([O:22][CH3:23])[CH:19]=2)[CH2:14][N:13]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:11]>C(OCC)C>[CH3:32][C:29]([O:28][C:26]([N:13]1[CH:12]([C:10]([OH:11])=[O:9])[CH2:21][C:20]2[C:15](=[CH:16][C:17]([O:24][CH3:25])=[C:18]([O:22][CH3:23])[CH:19]=2)[CH2:14]1)=[O:27])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 54558023HCID 54558023, compound

Product 1

HCID 170394272-(tert-Butoxycarbonyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidYield 101.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
8 °C

Procedure

Water (64 mg, 0.07 mL. 3.56 mmol) was added to a slurry of potassium t-butoxide (1.44 g, 12.8 mmol) in diethyl ether (25 mL) at 0° C. with stirring. After 5 minutes, the title B compound, 3,4-dihydro-6,7-dimethoxy-2,3(1H)-isoquinolinedicarboxylic acid 2-(1,1-dimethylethyl) 3-methyl ester (570 mg, 1.62 mmol) was added as a solution in 8 mL of ether. Stirring was continued for 45 minutes with warming to 8° C. after which the cooling bath was removed and stirring was continued at room temperature for 45 minutes. The reaction was quenched with 10 mL of saturated aqueous ammonium chloride, diluted with water, and extracted with ether. The aqueous solution was then acidified to pH 5 with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution was dried (sodium sulfate) and concentrated to give 554 mg of the title compound as a viscous yellow oil.

Workup

  1. stirringStirring
  2. waitwas continued for 45 minutes
  3. customwas removed
  4. stirringstirring
  5. waitwas continued at room temperature for 45 minutes
  6. customThe reaction was quenched with 10 mL of saturated aqueous ammonium chloride
  7. additiondiluted with water
  8. extractionextracted with ether
  9. extractionextracted with ethyl acetate
  10. dry with materialThe ethyl acetate solution was dried (sodium sulfate)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-a097546bf2a645cb8f8407ed1b90cf20
Source dataset
uspto-grants-2001_01
Patent number
US06172081B2

Reaction notes

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