Tetrabutylammonium Fluoride → Tert-butyl 4-hydroxy-4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate

Tetrabutylammonium fluoride (1M in tetrahydrofuran, 80 mL, 80 mmol) was added to a solution of 1,1-dimethylethyl 4-hydroxy-4-(3-trimethylsilyloxypropynyl)-1-piperidinecarboxylate (Description 71, 24.4 g, 75 mmol) in tetrahydrofuran (300 mL) and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure and water (200 mL) was added, The mixture was extracted with ethyl acetate (2×200 mL) and the combined organic fractions were washed with water (2×200 mL) and brine (200 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as an orange oil (16.8 g, 88%). 1H NMR (400 MHz, CDCl3) δ 4.32 (2H, s), 3.80–3.68 (2H, m), 3.32–3.22 (2H, m), 1.93–1.83 (2H, m), 1.75–1.65 (2H, m), 1.62 (1H, br s), and 1.46 (9H, s).

1. customThe solvent was evaporated under reduced pressure and water (200 mL)
2. additionwas added
3. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
4. washthe combined organic fractions were washed with water (2×200 mL) and brine (200 mL)
5. dry with materialdried (MgSO4)
6. customthe solvent was evaporated under reduced pressure

ORD record

ord-c48c63fd11b744b0880f21c3dee16e16

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105507B2