Sodium hydride → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate

Beteiligte Stoffe

Reaktionsschritte

Upon cooling a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(5-chloropentanamido)propan-2-ylcarbamate (500 mg, 1.18 mmol) in DMF (10 mL) to 0° C., NaH (52 mg, 1.30 mmol) was added. The reaction mixture was stirred for 4 h. The mixture was taken up in EtOAc, washed with saturated NaCl solution, dried over Na2SO4, concentrated under reduced pressure and the crude (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate was used in next step without purification (370 mg, 81%). 1H NMR (CDCl3, 300 MHz) δ 5.25 (d, 1H), 4.04-3.81 (m, 2H), 3.67-3.20 (m, 4H), 2.36 (m, 2H), 1.78 (m, 4H), 1.41 (s, 9H), 0.88 (s, 9H), 0.0 (s, 6H).

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