Lithium hydroxide, monohydrate → 2-((Tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid

HRID 1808376Notes

Reaction equation

HRID 1808376 reaction equation
O.[OH-].[Li+].C[C:5]1([C:22]([O-:24])=[O:23])[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]2)=[CH:7][CH2:6]1>O.CO>[C:18]([O:17][C:15]([N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][C:5]([C:22]([OH:24])=[O:23])=[CH:6][CH:7]=2)[CH2:12]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86645320HCID 86645320, compound

Product 1

HCID 189883742-((Tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide monohydrate (5.8 g, 0.136 mol) dissolved in water (73 ml) was added to a solution of 2-tert-butyl 7-methyl-3,4-dihydroisoquinoline-2,7(1H)-dicarboxylate (7.9 g, 0.027 mol) in methanol (110 ml), and the mixture was stirred for 4 h. The solvent was removed in vacuo. Water and diethyl ether were added to the residue, and the phases were separated. The aqueous phase was adjusted to an acidic pH with dilute aqueous HCl solution and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting crude product was used directly in the following stage. Yield: 5.8 g (76%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionWater and diethyl ether were added to the residue
  3. customthe phases were separated
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4cc49a2d6e44ecaa19fb04fae84abd6
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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