反应详情

To a stirred solution of 5-carboxymethyl-2-[(2S,4S)-1-tert-butoxycarbonyl-4-(2-napthyloxy)-2-pyrrolidinyl]methoxypyridine (170 mg, 0.36 mmol) in CH2Cl2 (5 ml) was added TFA (2 ml) at room temperature. After 2 h stirring, the mixture was concentrated in vacuo, which was diluted with CH2Cl2 and basified by the addition of 1 N NaOH. The combined reaction mixture was extracted with CH2Cl2. The organic layer was washed with brine, which were dried over NaSO4 and concentrated. The residue was purified on TLC [CHCl3/MeOH (10/1)], to give methyl 2-[(2S,4S)-4-(2-naphthyloxy)-2-pyrrolidinyl]methoxypyridine-5-carboxylate (107 mg, 80%) as a colorless oil 1H-NMR (CDCl3) δ1.95 (m, 1H), 2.27 (br, 1H), 2.46 (m, 1H), 3.19 (dd, J=12.2, 4.9 Hz, 1H), 3.41 (d, J=12.2 Hz, 1H), 3.65 (m, 1H), 3.89 (s, 3H), 4.58 (m, 2H), 5.00 (br, 1H), 6.77 (d, J=8.8 Hz, 1H), 7.06 (br, 1H), 7.11 (dd, J=8.8, 2.7 Hz, 1H), 7.31-7.45 (m, 2H), 7.69-7.76 (m, 3H), 8.13 (dd, J=8.8, 2.4 Hz, 1H), 8.78 (d, J=2.2 Hz, 1H).

1. concentrationthe mixture was concentrated in vacuo, which
2. additionwas diluted with CH2Cl2
3. additionbasified by the addition of 1 N NaOH
4. customThe combined reaction mixture
5. extractionwas extracted with CH2Cl2
6. washThe organic layer was washed with brine, which
7. dry with materialwere dried over NaSO4
8. concentrationconcentrated
9. customThe residue was purified on TLC [CHCl3/MeOH (10/1)]