반응 #61358

반응 방정식

water

Sodium hydride

Boc-4(R)-hydroxyproline

1-(bromomethyl) naphthalene

→

title compound

수율 56.2%

Boc-4(R)-(naphthalen-1-ylmethoxy)proline

수율 56.2%

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITION, (1981), 59, 2629-2641) was added
2. 2
   온도the mixture was heated
3. 3
   온도at reflux for 18 h
4. 4
   세척washed with hexane
5. 5
   추출extracted twice with ethyl acetate
6. 6
   세척washed with brine
7. 7
   건조dried (MgSO4)
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타The residue was purified by flash chromatography (49:49:2 hexane:ethyl acetate:acetic acid)

실험 절차

Commercially available Boc-4(R)-hydroxyproline (5.00 g, 21.6 mmol) was dissolved in THF (100 mL) and cooled to 0° C. Sodium hydride (60% dispersion in oil, 1.85 g, 45.4 mmol) was added portionwise over 10 minutes and the suspension was stirred at RT for 1 h. Then, 1-(bromomethyl) naphthalene (8.00 g, 36.2 mmol) (prepared as described in E. A. Dixon et al. Can. J. Chem., (1981), 59, 2629-2641) was added and the mixture was heated at reflux for 18 h. The mixture was poured into water (300 mL) and washed with hexane. The aqueous layer was acidified with 10% aqueous HCl and extracted twice with ethyl acetate. The organic layers were combined and washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (49:49:2 hexane:ethyl acetate:acetic acid) to give the title compound as a colorless oil (4.51 g, 56% yield). 1H NMR (DMSO-d6) indicated the presence of two rotamers: δ 8.05 (m, 1H), 7.94 (m, 1H), 7.29 (d, J=14 Hz, 1H), 7.55-7.45 (m, 4H), 4.96 (m, 2H), 4.26 (br. s, 1H), 4.12 (dd, J=8 Hz, 1H), 3.54-3.42 (m, 2H), 2.45-2.34 (m, 1H), 2.07-1.98 (m, 1H), 1.36 (s, (3/9) 9H), 1.34 (s, (6/9) 9H).

출처