反応 #2358501

反応方程式

(5R,6R,7S,8S)-6,7,8-Tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(1-octynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

→

title compound

(5R,6R,7S,8S)-5-Hydroxymethyl-2-n-octyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol

溶媒

THF EtOH

反応条件

後処理

1. 1
   ろ過After filtration of the catalyst
2. 2
   濃縮the organic solution is concentrated on a rotovap
3. 3
   workup.DISSOLUTIONthe residue is dissolved in CH2Cl2 (10 ml)
4. 4
   温度The solution is cooled in an acetone-dry ice bath
5. 5
   workup.ADDITIONa solution of BCl3 (1.0 M) in CH2Cl2 is slowly added
6. 6
   温度The reaction mixture is cooled in an ice-water bath
7. 7
   workup.ADDITIONwater added and for 0.5 hour
8. 8
   その他Most of the solvent is removed
9. 9
   その他the crude product is purified by chromatography (CHCl3/MeOH/H2O 64:25:4)

実験手順

A solution of (5R,6R,7S,8S)-6,7,8-Tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(1-octynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (120 mg, 0.179 mmol) in THF/EtOH (2:1) (3 ml) is rapidly stirred with Pd(OH)2/C (0.1 g) under an atmosphere of hydrogen for 14 h. After filtration of the catalyst, the organic solution is concentrated on a rotovap and the residue is dissolved in CH2Cl2 (10 ml). The solution is cooled in an acetone-dry ice bath and a solution of BCl3 (1.0 M) in CH2Cl2 is slowly added. The reaction mixture is warmed room temperature and stirred for 3 hours. The reaction mixture is cooled in an ice-water bath, water added and for 0.5 hour. Most of the solvent is removed using a rotovap and the crude product is purified by chromatography (CHCl3/MeOH/H2O 64:25:4). Lyophilization from water gives the title compound as white foam. 1H NMR (400 MHz, CD3OD): δ7.22 (s, 1H), 4.56 (d, 1H, J=8 Hz), 4.20-4.16 (m, 1H), 3.98-3.93 (m, 2H), 3.83 (t, 1H, J=8.4 Hz), 3.70 (dd, 1H, J=8.8 Hz and 10 Hz), 2.60 (t, 2H, J=7.2 Hz), 1.67-1.63 (m, 2H), 1.35-1.30 (m, 10H), 0.90 (t, 3H, J=6.8 Hz). MS (ES+): 313 [M+1].

出典