反応 #1790370

反応方程式

Ethyl 1-aminocyclopropanecarboxylate hydrochloride

1,2-bis(bromomethyl)naphthalene

potassium carbonate

→

title compound

収率 22.1%

2-(1'-Hydroxymethylcyclopropyl)benz[e]isoindoline hydrochloride

収率 22.1%

溶媒

chloroform

chloroform

反応条件

後処理

1. 1
   その他kept at 60°
2. 2
   温度The reaction mixture was refluxed for a further 6 hr
3. 3
   ろ過filtered
4. 4
   その他the filtrate was evaporated to dryness
5. 5
   workup.DISSOLUTIONthe residue [i.e. crude 2-(1'-carbethoxycyclopropyl)benz[e]isoindoline] was dissolved in THF (150 ml)
6. 6
   workup.ADDITIONadded to lithium aluminium hydride (10 g) in THF (100 ml) over 0.5 h
7. 7
   workup.ADDITIONWater was then added
8. 8
   ろ過the resultant slurry was filtered
9. 9
   その他the filtrate was evaporated to dryness
10. 10
    その他the residue was partitioned between ether and water
11. 11
    抽出the ether layer was extracted with concentrated hydrochloric acid
12. 12
    抽出The acidic extract
13. 13
    その他was evaporated to dryness
14. 14
    その他to give a residue which
15. 15
    その他was recrystallised from iso-propanol/ethyl acetate

実験手順

Ethyl 1-aminocyclopropanecarboxylate hydrochloride (16 g) in chloroform (50 ml) was added to 1,2-bis(bromomethyl)naphthalene (40 g) and potassium carbonate (40 g) in chloroform (200 ml) kept at 60°. The reaction mixture was refluxed for a further 6 hr and then filtered; the filtrate was evaporated to dryness and the residue [i.e. crude 2-(1'-carbethoxycyclopropyl)benz[e]isoindoline] was dissolved in THF (150 ml) and added to lithium aluminium hydride (10 g) in THF (100 ml) over 0.5 h. Water was then added and the resultant slurry was filtered and the filtrate was evaporated to dryness; the residue was partitioned between ether and water and the ether layer was extracted with concentrated hydrochloric acid. The acidic extract was evaporated to dryness to give a residue which was recrystallised from iso-propanol/ethyl acetate to give the title compound (5.9 g. m.p.192°).

出典