Water → 2-(Tert-butoxycarbonyl)-6-(methoxymethyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

HRID 2202285Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]([C:14]([O:16]CC)=[O:15])[N:9]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:8][CH2:7]2.C1COCC1.O.[OH-].[Li+]>CO>[C:22]([O:21][C:19]([N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][CH:13]=[C:4]([CH2:3][O:2][CH3:1])[CH:5]=2)[CH:10]1[C:14]([OH:16])=[O:15])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-ethyl 2-tert-butyl 6-(methoxymethyl)-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate (160 mg, 0.0.46 mmol) in a mixture of MeOH (5 mL), THF (5.00 mL) and water (5.00 mL) was added lithium hydroxide (65.8 mg, 2.75 mmol), and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in water, and the solution was washed with ethyl acetate. The pH of the aqueous layer was adjusted to 3 with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give 2-(tert-butoxycarbonyl)-6-(methoxymethyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (148 mg, 0.461 mmol, 101%) as a colorless amorphous solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionThe obtained residue was dissolved in water
washthe solution was washed with ethyl acetate
extractionthe mixture was extracted with ethyl acetate (×3)
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-b6d6a0b5997c41258a7500968bbe58c6
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365520B2

Reaction notes

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