反应详情

Dimethylamine (5.6 M solution in EtOH, 0.28 ml, 1.53 mmol) is added under an atmosphere of argon to a solution of (2-chloro-6-formyl-naphthalen-1-yl)-acetic acid ethyl ester (284 mg, 1.02 mmol) in THF (10 ml). The mixture is stirred at RT for 18 h, before a solution of sodium cyanoborohydride (78 mg, 1.23 mmol) in MeOH (2 ml) and glacial acetic acid (0.29 ml, 5.13 mmol) are added. After stirring at RT for 1 h, TLC analysis indicates complete consumption of starting material. The reaction mixture is diluted with water and adjusted to pH 8-9 by the addition of conc. aq. NaHCO3 solution. Extraction with EtOAc, washing with brine, drying over Na2SO4 and removal of solvent yields the crude reaction product. Purification by FCC (CH2Cl2/EtOH/NH3 190:9:1) affords the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.26 (t, J=9 Hz, 3H), 2.30 (s, 6H), 3.59 (s, 2H), 4.18 (q, J=9 Hz, 2H), 4.30 (s, 2H), 7.49 (d, J=10 Hz, 1H), 7.54-7.58 (m, 1H), 7.69-7.76 (m, 2H), 7.91 (d, J=10 Hz, 1H). ES+-MS: 306.4, 308.3 [M+H]+.

1. additionare added
2. customconsumption of starting material
3. additionThe reaction mixture is diluted with water
4. additionadjusted to pH 8-9 by the addition of conc. aq. NaHCO3 solution
5. extractionExtraction with EtOAc
6. washwashing with brine
7. dry with materialdrying over Na2SO4 and removal of solvent
8. customyields the crude
9. customreaction product
10. customPurification by FCC (CH2Cl2/EtOH/NH3 190:9:1)