반응 #837216

반응 방정식

product

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

2,4-dichloro-benzyl chloride

Cs2CO3

→

title product

수율 57.5%

(R)-2-[4-(2,4-Dichloro-benzyloxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

수율 57.5%

용매

DMF

반응 조건

후처리

1. 1
   기타The reaction mixture which resulted
2. 2
   추출extracted with EtOAc (3×30 mL)
3. 3
   세척The combined organic layers were washed with water (30 mL) and brine (30 mL)
4. 4
   기타dried over anhy
5. 5
   기타The solvent was removed under vacuo
6. 6
   기타to obtain the crude product which
7. 7
   기타was purified by silica gel flash chromatography

실험 절차

To a 25 mL vial which contained a solution of the product from step 1 (150 mg, 0.5 mmol) and 2,4-dichloro-benzyl chloride (180 mg, 0.8 mmol) in anhydrous DMF (15 mL) was added dry Cs2CO3 (150 mg, 0.75 mmol) at rt. The reaction mixture which resulted was allowed to stir at rt for 7 d. The mixture was poured onto 50 mL ice-water solution and extracted with EtOAc (3×30 mL) allowed). The combined organic layers were washed with water (30 mL) and brine (30 mL) and dried over anhy. Na2SO4. The solvent was removed under vacuo to obtain the crude product which was purified by silica gel flash chromatography to afford the title product (130 mg, 55%); 1H NMR (400 MHz, CDCl3); δ 1.47 (s, 9H), 1.80-2.10 (m, 4H), 3.26-3.45 (m, 2H), 3.69-3.91 (m, 1H), 4.01-4.18 (m, 2H), 5.07 (s, 2H), 6.84-6.90 (m, 4H), 7.25-7.28 (m, 1H), 7.41 (d, J=2.0 Hz, 1H), 7.49 (d, J=8.4 Hz, 1H),

출처