Lithium Hydroxide → HCID 59490563, compound

HRID 2383487Notes

Reaction equation

HRID 2383487 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH:17]([C:21]([O:23]CC)=[O:22])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[OH-].[Li+]>O1CCCC1.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH:17]([C:21]([OH:23])=[O:22])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:26][CH:27]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 59490482HCID 59490482, compound

Product 1

HCID 59490563HCID 59490563, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinoline-7-carboxylate (159 mg, 0.44 mmol) in tetrahydrofuran (5 mL), methanol (2 mL) and water (3 mL) was added excess lithium hydroxide (0.5 g). The mixture was stirred at room temperature for 1.5 hours diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The organic layer was dried with anhydrous magnesium sulfate and evaporated to dryness to give 3-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinoline-7-carboxylic acid as an off white solid (157 mg). 1H NMR (DMSO-d6) 400 MHz δ 12.33 (brs, 1H), 8.02 (s, 1H), 7.95 (s, 1H), 7.16 (d, J=8.0 Hz, 2H), 6.84 (d, J=8.0 Hz, 2H), 5.52 (s, 2H), 3.69 (s, 3H), 3.14-2.97 (m, 4H), 2.82-2.74 (m, 1H), 2.22-2.14 (m, 1H), 1.97-1.87 (m, 1H); LCMS [M+H]: 338.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-bfee918717d4424484a1f1b1dc97656a
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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