2-(2,3,3a,8b-Tetrahydrocyclopenta[b]Indol-4(1H)-yl)Acetamide → 2-(2,3,3a,8b-Tetrahydrocyclopenta[b]indol-4(1h)-yl)ethylamine

HRID 1836102Notes

Reaction equation

HRID 1836102 reaction equation
[CH2:1]1[CH:12]2[CH:4]([N:5]([CH2:13][C:14]([NH2:16])=O)[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=32)[CH2:3][CH2:2]1>B.C1COCC1>[CH2:1]1[CH:12]2[CH:4]([N:5]([CH2:13][CH2:14][NH2:16])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=32)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 218735702-(2,3,3a,8b-Tetrahydrocyclopenta[b]Indol-4(1H)-yl)Acetamide

Product 1

HCID 113216342-(2,3,3a,8b-Tetrahydrocyclopenta[b]indol-4(1h)-yl)ethylamine

Reagents, catalysts & solvents 1

HCID 2723981Borane;tetrahydrofuranSolvent

Procedure

2-(2,3,3a,8b-Tetrahydrocyclopenta[b]indol-4(1H)-yl)acetamide (90 mmol, 20 g) was dissolved in 1 M BH3.THF (200 mL) and heated to reflux for 18 h. The reaction mixture was allowed to cool to room temperature and then quenched slowly with methanol. The solution was concentrated, dissolved in methanol, and again concentrated. The resulting oil was diluted with ether and extracted twice with 1 N HCl. The aqueous phase was treated with 2.5 N NaOH to pH>10 and extracted with chloroform. The combined chloroform extracts were dried over MgSO4, filtered and concentrated to provide a yellow oil which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 h
  3. customquenched slowly with methanol
  4. concentrationThe solution was concentrated
  5. dissolutiondissolved in methanol
  6. concentrationagain concentrated
  7. additionThe resulting oil was diluted with ether
  8. extractionextracted twice with 1 N HCl
  9. additionThe aqueous phase was treated with 2.5 N NaOH to pH>10
  10. extractionextracted with chloroform
  11. dry with materialThe combined chloroform extracts were dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customto provide a yellow oil which
  15. customwas used without further purification

Sources & evidence

ORD record
ord-5aacc814fa2843e0a16eaff52b378b11
Source dataset
uspto-grants-2004_08
Patent number
US06777407B2

Reaction notes

Loading…