Aluminium lithium hydride → (2S,4S)-tert-butyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

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Reaction Steps

To a solution of lithium aluminum hydride, 1.0 M solution in tetrahydrafuran (1.165 mL, 1.165 mmol) in 7 mL THF at 0° C. was added a solution of (S)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-1H-pyrrole-1,2(2H,5H)-dicarboxylate (0.555 g, 0.971 mmol) dropwise via syringe, over 5 min. The reaction mixture became a deep purple color. The bath was removed, and after 30 min, the reaction mixture was re-cooled, and treated with ice carefully. 6 mL 1N aq. HCl was added and the aq. Layer was extracted with DCM. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel chromatography, 0-100% EA/hexanes gradient gave (2S,4S)-tert-butyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate. MS (ESI) m/z: Calculated: 545.2; Observed: 546.1 (M++1).

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