Ammonium Chloride → HCID 58456731, compound

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Reaction Steps

In a plastic container, a solution of tert-butyl 4-(3,5-difluoro-4-hydroxyphenyl)-4-hydroxypiperidine-1-carboxylate D1f (0.4 g, 1.2 mmol) in dichloromethane (10 mL) is treated with DAST (0.31 mL, 2.4 mmol) at room temperature. The mixture is stirred for 30 min and treated with sat. aqueous NH4Cl (3 mL). The mixture is extracted with dichloromethane, washed with sat. aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo to yield tert-butyl 4-(3,5-difluoro-4-hydroxyphenyl)-4-fluoropiperidine-1-carboxylate D1g as an oil. 1H-NMR (400 MHz, CDCl3) δ=7.01 (d, J=7.2 Hz, 2H), 4.03 (br. s, 2H), 3.19 (br. s, 2H), 1.88 td, J=13.3, 4.8 Hz, 2H), 1.66 (dq, J=14.1, 2.2 Hz, 2H), 1.47 (s, 9H); 19F-NMR (376 MHz, CDCl3) δ=−134.1 (2F), −161.9 (1F). LCMS calcd. for C16H21F3NO3+ ([M+H]+): 332.1, found: 331.8. The product is used without purification.

Provenance & Evidence