Dicyclohexylcarbodiimide → 3-(3-Pyridyl)-1-propyl (2s)-n-(tert-butyloxycarbonyl)-pyrrolidine-2-carboxylate

A mixture of N-(tert-butyloxycarbonyl)-(S)-proline (3.0 g; 13.9 mmol); 3-(3-Pyridyl)-1-propanol (2.90 g; 20.9 mmol), dicyclohexylcarbodiimide (4.59 g; 22.24 mmol), camphorsulfonic acid (1.08 g; 4.63 mmol), and 4-dimethylaminopyridine (0.60 g; 4.63 mmol) in dry methylene chloride (100 mL) was stirred overnight. The reaction mixture was diluted with methylene chloride (50 mL) and water (100 mL), and the layers were separated. The organic phase was washed with water (3×100 mL), dried over magnesium sulfate, and concentrated, and the crude residue was purified on a silica gel column eluting with ethyl acetate to obtain 4.60 g (95%) of the ester as a thick oil, 1H NMR (300 MHz, CDCl3): δ 1.45 (s, 9H); 1.70-2.05 (m, 5H); 2.32 (m, 1H); 2.71 (t, 2H); 3.50 (m, 2H); 4.15 (m, 2H); 4.18 (m, 1H); 7.24 (m, 1H); 7.51 (m, 1H); 8.48 (m, 2H).

1. customthe layers were separated
2. washThe organic phase was washed with water (3×100 mL)
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated
5. customthe crude residue was purified on a silica gel column
6. washeluting with ethyl acetate

ORD 기록

ord-b50b937792d14c7ba5f71f089a3798d9

출처 데이터셋

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06242468B1