Lithium Hydroxide → HCID 10364529, compound

HRID 2111996Notes

Reaction equation

HRID 2111996 reaction equation
[OH-].[Li+].[CH2:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]1[C:13](=[O:34])[CH2:14][CH2:15][C:16]1[CH:33]=[CH:32][C:19]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26]C)=[O:25])=[CH:18][CH:17]=1>O.C1COCC1>[CH2:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]1[C:13](=[O:34])[CH2:14][CH2:15][C:16]1[CH:33]=[CH:32][C:19]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68870373HCID 68870373, compound

Product 1

HCID 10364529HCID 10364529, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (14.4 mg, 0.6 mmol) dissolved in water (1 ml) was added into 70377 methyl 2-({4-[3-(3,4-dihydroisoquinolin-2(1H)-yl)-3-oxopropyl]phenoxy}methyl)benzoate (129 mg, 0.3 mmol) in THF (2 ml). The mixture was put in a microwave oven (Smith Synthesizer) and irradiated at 150° C. for 7 minutes and then evaporated to remove THF. The residue was acidified with 1% hydrochloric acid, pH˜5, and extracted with ethyl acetate (×2). The extracts were combined and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM, MeOH/DCM (1:99) as eluant gave 111 mg the desired product yield 89%.

Workup

  1. customThe mixture was put in a microwave oven
  2. custom(Smith Synthesizer) and irradiated at 150° C. for 7 minutes
  3. customevaporated
  4. customto remove THF
  5. extractionextracted with ethyl acetate (×2)
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated

Sources & evidence

ORD record
ord-485161a4f2da45a48d2ad1a7b0e55d11
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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