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

HRID 1703188ノート

反応式

HRID 1703188 の反応式
[ClH:1].[NH2:2][C:3]1([C:6]([O:8]CC)=O)[CH2:5][CH2:4]1.Br[CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[CH2:23]Br.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[ClH:1].[OH:8][CH2:6][C:3]1([N:2]2[CH2:12][C:13]3[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[CH:16]=[CH:15][C:14]=3[CH2:23]2)[CH2:4][CH2:5]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 386203Ethyl 1-aminocyclopropane-1-carboxylate hydrochlorideHCID 34035511,2-Bis(bromomethyl)naphthalene

生成物 1

HCID 129537822-(1'-Hydroxymethylcyclopropyl)benz[e]isoindoline hydrochloride収率 22.1%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

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°).

後処理

  1. customkept at 60°
  2. temperatureThe reaction mixture was refluxed for a further 6 hr
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness
  5. dissolutionthe residue [i.e. crude 2-(1'-carbethoxycyclopropyl)benz[e]isoindoline] was dissolved in THF (150 ml)
  6. additionadded to lithium aluminium hydride (10 g) in THF (100 ml) over 0.5 h
  7. additionWater was then added
  8. filtrationthe resultant slurry was filtered
  9. customthe filtrate was evaporated to dryness
  10. customthe residue was partitioned between ether and water
  11. extractionthe ether layer was extracted with concentrated hydrochloric acid
  12. extractionThe acidic extract
  13. customwas evaporated to dryness
  14. customto give a residue which
  15. customwas recrystallised from iso-propanol/ethyl acetate

出典と根拠

ORDレコード
ord-d7cdea20c5a544d8a49eddbf2ff40456
出典データセット
uspto-grants-1982_09
特許番号
US04351842

反応ノート

読み込み中…