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

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).

1. customTo a 250 mL round bottomed flask which contained
2. customThe stirred solution was flushed with a H2 balloon
3. filtrationThe reaction mixture was then filtered
4. washwashed with THF (30 ml), EtOH (25 ml)
5. customdried in vacuo
6. customto provide the crude product which
7. customwas further purified by recrystallization with ether-EtOAc-hexane

ORD record

ord-6c6666ea8aaf4ebfa7b39f949aa0b153

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402684B2