反応 #40649

反応方程式

aminoalcohol

4-[1-Amino-2-(4-fluorophenyl)-ethyl]-4-hydroxypiperidine-1-carboxylic acid benzyl ester

NaI

chloroacetylchloride

iodide

tert-butoxide

→

title compound

収率 19.0%

5-(4-Fluorobenzyl)-3-oxo-1-oxa-4,9-diaza-spiro[5.5]undecane-9-carboxylic acid benzyl ester

収率 19.0%

反応条件

後処理

1. 1
   その他Purification of the crude product by silica gel column chromatography
2. 2
   洗浄eluting with a stepwise gradient of 0-100% ethyl acetate in n-heptane

実験手順

The title compound was prepared from aminoalcohol 103NLS28 (303 mg, 0.81 mmol) according to literature procedures (Clark et al., J. Med. Chem. 26:855-861 (1983)), by acylation of the amino function with chloroacetylchloride, followed by halogen exchange with NaI and ring closure of the iodide derivative in presence of tert-butoxide. Purification of the crude product by silica gel column chromatography, eluting with a stepwise gradient of 0-100% ethyl acetate in n-heptane, afforded the title compound (64 mg, 19% overall yield) as a colourless solid.

出典