反应详情

To a stirred solution of the 1,2,3,4-Tetrahydro-quinoline-3-carboxylic acid methyl ester (93 mg, 0.49 mmol) in 1.5 mL of Et2O at 0° C. under nitrogen was added LiA1H4 (1M in Et2O) dropwise with vigorous gas evolution and a white precipitate formation. After 30 min., the reaction was carefully quenched with 15% NaOH (3 mL) and 3 mL of Et2O was added and the mixture stirred rapidly at RT for 15 min. The layers were separated and the aqueous layer extracted (1×10 mL) with Et2O. The organics were combined, dried (MgSO4), filtered and concentrated to the alcohol (64 mg, 80%). 1H-NMR (400 MHz, CDCl3) δ6.97 (m, 2H), 6.62 (dd, 1H), 6.47 (d, 1H), 3.66 (m, 1H), 3.58 (m, 1H), 3.40 (m, 1H), 3.08 (m, 1H), 2.82 (m, 1H), 2.53 (m, 1H), 2.18 (m, 1H).

1. customthe reaction was carefully quenched with 15% NaOH (3 mL) and 3 mL of Et2O
2. additionwas added
3. customThe layers were separated
4. extractionthe aqueous layer extracted (1×10 mL) with Et2O
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated to the alcohol (64 mg, 80%)