반응 #837255

반응 방정식

NaOH

2-(4-phenylacetyl-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

triethylsilane

→

title product

수율 82.0%

(R)-2-(4-Phenethyl-phenoxymethyl)-pyrrolidine

수율 82.0%

용매

TFA

반응 조건

후처리

1. 1
   추출extracted with EtOAc (3×20 mL)
2. 2
   세척The combined organic layers were washed with water (2×20 mL) and brine (20 mL)
3. 3
   기타dried over anhy
4. 4
   기타The solvent was removed in vacuo
5. 5
   기타to obtain the crude product which
6. 6
   기타was purified by silica gel flash chromatography

실험 절차

To a solution of R)-2-(4-phenylacetyl-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (40 mg, 0.16 mmol) in TFA (1.0 mL) was added triethylsilane (0.2 mL, 0.9 mmol) at 0° C. The resulting mixture was allowed to warm to rt and stir at rt for 16 h. The mixture was poured onto 20 mL ice-water solution, neutralized with aq NaOH (2N) to pH=6-7, and then extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (2×20 mL) and brine (20 mL) and dried over anhy. Na2SO4. The solvent was removed in vacuo to obtain the crude product which was purified by silica gel flash chromatography to afford the title product (25 mg, 82%); LCMS; 99%, ESI+, Calcd: 281.4. Found m/z: 282.6 M+1). 1H NMR (400 MHz, CDCl3,); δ 1.54-1.61 (m, 1H), 1.74-1.84 (m, 2H), 1.90-1.99 (m, 1H), 2.84-3.07 (m, 6H), 3.49-3.52 (m, 1H), 3.83-3.92 (m, 2H), 6.82 (d, J=8.8 Hz, 2H), 7.07 (d, J=8.8 Hz, 2H), 7.16-7.20 (m, 3H)-7.34 (m, 2H).

출처