반응 #837215

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

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title product

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

용매

EtOH

THF

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후처리

1. 1
   기타To a 250 mL round bottomed flask which contained
2. 2
   기타The stirred solution was flushed with a H2 balloon
3. 3
   여과The reaction mixture was then filtered
4. 4
   세척washed with THF (30 ml), EtOH (25 ml)
5. 5
   기타dried in vacuo
6. 6
   기타to provide the crude product which
7. 7
   기타was further purified by recrystallization with ether-EtOAc-hexane

실험 절차

To a 250 mL round bottomed flask which contained a suspension of Pd—C (10% wt 3 g) in EtOH (70 mL) and THF (30 mL) was added (R)-2-(4-benzyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.5 g, 9 mmol). The stirred solution was flushed with a H2 balloon. This process was repeated 3 times. The resulting solution was stirred at rt under hydrogen atmosphere overnight. The reaction mixture was then filtered, washed with THF (30 ml), EtOH (25 ml) and dried in vacuo to provide the crude product which was further purified by recrystallization with ether-EtOAc-hexane to yield the title product, (2.5, 90%); MS; APCI+, Calcd: 293.5. Found m/z: 294.2 (M+1). 1H NMR (400 MHz, CDCl3); δ 1.47 (s, 9H), 1.80-2.10 (m, 4H), 3.40 (br, 2H), 3.69-3.89 (m, 1H), 4.00-4.18 (m 2H), 6.71-6.76 (m, 4H).

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