반응 #592377

반응 방정식

sodium cyanoborohydride

acetic acid

2-Fluoroethylamine hydrochloride

(2-chloro-7-formyl-naphthalen-1-yl)-acetic acid ethyl ester

Triethylamine

→

title compound

(7-{[(2-fluoro-ethyl)-amino]-methyl}-2-chloro-naphthalen-1-yl)-acetic acid ethyl ester

용매

MeOH

THF

반응 조건

후처리

1. 1
   workup.ADDITIONare added
2. 2
   기타consumption of starting material
3. 3
   workup.ADDITIONThe reaction mixture is diluted with water
4. 4
   workup.ADDITIONadjusted to pH 8 by the addition of a 1 M aqueous solution of NaHCO3
5. 5
   추출Extraction with EtOAc
6. 6
   세척washing with brine
7. 7
   건조drying over Na2SO4 and removal of solvent
8. 8
   기타yields the crude
9. 9
   기타reaction product
10. 10
    기타Purification by FCC (EtOAc/MeOH 9:1)

실험 절차

2-Fluoroethylamine hydrochloride (94 mg, 0.94 mmol) is added under an atmosphere of argon to a solution of (2-chloro-7-formyl-naphthalen-1-yl)-acetic acid ethyl ester (200 mg, 0.72 mmol) in 7.6 ml of THF. Triethylamine (0.13 ml, 0.94 mmol) is added, and the mixture is stirred at RT for 18 h, before a solution of sodium cyanoborohydride (50 mg, 0.80 mmol) in MeOH (2.0 ml) and glacial acetic acid (0.21 ml, 3.61 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 by the addition of a 1 M aqueous solution of NaHCO3. Extraction with EtOAc, washing with brine, drying over Na2SO4 and removal of solvent yields the crude reaction product. Purification by FCC (EtOAc/MeOH 9:1) affords the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.26 (t, J=8.4 Hz, 3H), 2.92-3.04 (m, 2H), 4.06 (s, 2H), 4.19 (q, J=8.4 Hz, 2H), 4.32 (s, 2H), 4.52-4.68 (m, 2H), 7.48 (d, J=9 Hz, 1H), 7.51-7.53 (m, 1H), 7.73 (d, J=9.4 Hz, 1H), 7.82 (d, J=9 Hz, 1H), 7.88 (s, 1H). ES+-MS: 324.2, 326.1 [M+H]+.

출처