Potassium Carbonate → tert-Butyl 3-ethynylpiperidine-1-carboxylate

A solution of 1-BOC-3-formylpiperidine (1.46 g, 6.85 mmol) and (diazomethyl) phosphonic acid dimethyl ester (1.79 g, 11.94 mmol) in 50 mL methanol was stirred at ice-bath for 10 min, K2CO3 (1.96 g, 14.2 mmol) was added to the above mixture and stirred at ice-bath for 2 hrs, then stirred at rt overnight. The mixture was evaporated in vacuo, to the residue was added EtOAc and water, the organic layer was separated and water layer was extracted with EtOAc (100 mL×3). The combined organic layers were washed with water and brine successively, dried with Na2SO4, filtered, and the filtrate was evaporated in vacuo to give 1.44 g product as colorless oil (100.0%). 1H NMR (300 MHz, CDCl3) δ: 3.90 (1 H, brs), 3.70-3.75 (1 H, m), 2.95-3.02 (2 H, m), 2.40-2.47 (1 H, m), 2.05 (1 H, d, J=2.1 Hz), 1.94-1.99 (1 H, m), 1.69-1.73 (1 H, m), 1.50-1.63 (2 H, m), 1.46 (9 H, s).

1. stirringstirred at rt overnight
2. customThe mixture was evaporated in vacuo, to the residue
3. additionwas added EtOAc and water
4. customthe organic layer was separated
5. extractionwater layer was extracted with EtOAc (100 mL×3)
6. washThe combined organic layers were washed with water and brine successively
7. dry with materialdried with Na2SO4
8. filtrationfiltered
9. customthe filtrate was evaporated in vacuo

ORD 기록

ord-32f7a68dc27044bbbc74af035265a9c7

출처 데이터셋

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09174996B2