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To a mixture of Compound 3 (14 g, 61 mmol) in MeOH/THF (300 mL/50mL) was added NaBH4 (3.4 g, 90 mmol) at 0 C , and stirred at rt overnight. 1 N HCl was added slowly to quenched the reaction. The mixture was concentrated in vacuo, and and the mixture was extracted with EtOAc (500 mLx3). The organic layer was concentrated to give the crude product, which was purified by column chromatography to give the compound 4 (8.0 g, 57 %). LCMS: 236.1 [M+l].
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Reference:
Patent; NOVIRA THERAPEUTICS, INC.; HARTMAN, George D.; FLORES, Osvaldo A.; WO2013/96744; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem