Methanol → HCID 66889007, compound

HRID 1895554Notes

Reaction equation

HRID 1895554 reaction equation
[CH3:1][C:2]1([C:22]([O:24]C)=[O:23])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[OH-].[Li+].CO>C1COCC1.O>[CH2:15]([O:14][C:12]([N:3]1[C:2]([CH3:1])([C:22]([OH:24])=[O:23])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 66872729HCID 66872729, compound

Product 1

HCID 66889007HCID 66889007, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Step-3: To a solution of 2-benzyl 3-methyl 3-methyl-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate in THF (1.2 mL) was added lithium hydroxide (50.5 mg, 1.204 mmol) in water (0.6 mL). Methanol (0.72 mL) was added till homogeneous solution was obtained and the reaction was heated at 60° C. overnight. The reaction was concentrated, acidified to pH 2 using 2 N HCl, extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated to afford the crude product which was purified by preparative TLC using hexane/ethyl acetate mixture (1:1) to afford 2-((benzyloxy)carbonyl)-3-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. MS (ES+): m/z 326.15 [M+H]+

Workup

  1. customwas obtained
  2. concentrationThe reaction was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customto afford the crude product which
  8. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-e97e265c9bf643a5b46f0af9be955036
Source dataset
uspto-grants-2013_08
Patent number
US08513433B2

Reaction notes

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