Lithium Hydroxide → 2-[2-(4-Cyclobutyl-piperazin-1-yl)-2-oxo-ethyl]-1,2,3,4-tetrahydro-isoquinoline-6-carboxylic acid

HRID 1713104Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][N:11]([CH2:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([CH:25]3[CH2:28][CH2:27][CH2:26]3)[CH2:21][CH2:20]1)=[O:18])[CH2:10][CH2:9]2)=[O:5])C.[OH-].[Li+]>C1COCC1.CO.O>[CH:25]1([N:22]2[CH2:21][CH2:20][N:19]([C:17](=[O:18])[CH2:16][N:11]3[CH2:10][CH2:9][C:8]4[C:13](=[CH:14][CH:15]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=4)[CH2:12]3)[CH2:24][CH2:23]2)[CH2:26][CH2:27][CH2:28]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-[2-(4-cyclobutyl-piperazin-1-yl)-2-oxo-ethyl]-1,2,3,4-tetrahydro-isoquinoline-6-carboxylic acid ethyl ester (610 mg, 1.58 mmol) in a mixture of THF-MeOH-water (3:1:1, 5 ml) cooled to 0° C. is added lithium hydroxide (76 mg, 3.16 mmol, 2.0 eq.). The mixture is stirred at rt overnight. The organic solvent is evaporated, and the residue is acidified to pH=5 with hydrochloric acid (2.0 N, about 1.58 ml). The resulting aqueous solution is evaporated to dryness, and the residue is extracted with a DCM-EtOH mixture (9:1, 10 ml×4). The combined organic solution is dried over sodium sulfate, and concentrated to give the title compound. MS (+VE) m/z 356.2 (M++1).

Workup

customThe organic solvent is evaporated
customThe resulting aqueous solution is evaporated to dryness
extractionthe residue is extracted with a DCM-EtOH mixture (9:1, 10 ml×4)
dry with materialThe combined organic solution is dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-d8b0d8a026344fbcacf08cbe8614a5c0
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795262B2

Reaction notes

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