Methyltriphenylphosphonium iodide → 3-Methylene-piperidine-1-carboxylic acid tert-butyl ester

A suspension of methyltriphenylphosphonium iodide (15.22 g, 37.6 mmol, Sigma-Aldrich) in THF (75 mL) was stirred at RT before addition of potassium t-butoxide (4.22 g, 37.6 mmol, Sigma-Aldrich) in one portion. The resulting bright yellow solution was stirred at RT for 30 minuets before adding tert-butyl 3-oxopiperidine-1-carboxylate (3 g, 15.06 mmol) and stirring for 3 h. It was poured into ice water, and the mixture was extracted with DCM (4×50 mL) before drying the combined organics over Na2SO4, filtering, and concentrating under reduced pressure. The crude material was purified by column chromatography (eluant: 0 to 10% EtOAc/hexanes), affording the product as a clear oil (1.93 g, 65%). 1H NMR (DMSO-d6) δ: 4.70-4.81 (m, 2H), 3.80 (s, 2H), 3.30-3.40 (m, 2H), 2.18-2.26 (m, 2H), 1.47-1.56 (m, 2H), 1.38 (s, 9H)

1. stirringstirring for 3 h
2. extractionthe mixture was extracted with DCM (4×50 mL)
3. dry with materialbefore drying the combined organics over Na2SO4
4. filtrationfiltering
5. concentrationconcentrating under reduced pressure
6. customThe crude material was purified by column chromatography (eluant: 0 to 10% EtOAc/hexanes)

ORD record

ord-5d00a7fc439c403cbfbd56fe2ae33be2

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090593B2