Dichloromethane → Ammonia dichloromethane

A suspension of tert-butyl 4-hydroxy-1-piperidine carboxylate (497 mg), 4-phenylphenol (300 mg), and polymer-supported triphenylphosphine (1.2 g) in DCM (10 mL) was treated with di-tert-butyl azodicarboxylate (608 mg). The resulting mixture was shaken for 16 h, and filtered through a pad of celite. The pad was washed with DCM (3×5 mL) and the combined filtrates were evaporated. The residue was dissolved in dioxane (5 mL) and treated with hydrogen chloride (5 mL of a 4 N solution in dioxane). After 16 h, solvent was removed and the residue was treated with 10% aqueous sodium hydroxide (20 mL). The resulting mixture was extracted with DCM (2×500 mL), and the combined organic phases were dried (magnesium sulfate) and evaporated. Chromatography of the residue (1–6% 2M methanolic ammonia/DCM) gave the title compound as a white solid (107 mg). 1H NMR (400 MHz, CDCl3): 7.56–7.49 (m, 4H), 7.42–7.39 (m, 2H), 7.31–7.27 (m, 1H), 6.99–6.96 (m, 2H), 4.43–4.37 (m, 1H), 3.18–3.13 (m, 3H), 2.77–2.70 (m, 2H), 2.07–2.01 (m, 2H), 1.73–1.64 (m, 2H).

1. filtrationfiltered through a pad of celite
2. washThe pad was washed with DCM (3×5 mL)
3. customthe combined filtrates were evaporated
4. dissolutionThe residue was dissolved in dioxane (5 mL)
5. additiontreated with hydrogen chloride (5 mL of a 4 N solution in dioxane)
6. waitAfter 16 h
7. customsolvent was removed
8. additionthe residue was treated with 10% aqueous sodium hydroxide (20 mL)
9. extractionThe resulting mixture was extracted with DCM (2×500 mL)
10. dry with materialthe combined organic phases were dried (magnesium sulfate)
11. customevaporated

ORD record

ord-bc54e3371c894b01a4870b31a5b802f5

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07241778B2