Propargylamine → HCID 19003106, compound

HRID 488094Notes

Reaction equation

HRID 488094 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12](=O)[CH2:13][CH2:14][C:5]=3[C:4]=2[CH:3]=1.[CH2:16]([NH2:19])[C:17]#[CH:18]>C(#N)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:11][N:7]1[C:8]2[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][C:4]=2[C:5]2[CH2:14][CH2:13][C:12](=[N:19][CH2:16][C:17]#[CH:18])[C:6]1=2

Participants

5

Reactant 2

HCID 239041PropargylamineHCID 15818737HCID 15818737, compound

Product 1

HCID 19003106HCID 19003106, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 7-hydroxy-4-methyl-1,4-dihydrocyclopent[b]indol-3(2H)-one (5.5 g) in acetonitrile (100 ml) was added propargyl amine (3.0 g), the solution was stirred at room temperature under a nitrogen atmosphere while titanium (IV) isopropoxide (15.6 g) was added in a dropwise manner. The mixture was stirred for 16 hours before quenching with ice water. The mixture was filtered, the solids were washed with CH2Cl2, the layers were separated and the organic portion was dried (Na2SO4). After concentration, the crude product was purified via flash chromatography eluting with hexane/acetone (2: 1) to give 4-methyl-3-(2-propynyl)imino-1,2,3,4-tetrahydrocyclopent[b]indol-7-ol.

Workup

  1. additionwas added in a dropwise manner
  2. custombefore quenching with ice water
  3. filtrationThe mixture was filtered
  4. washthe solids were washed with CH2Cl2
  5. customthe layers were separated
  6. dry with materialthe organic portion was dried (Na2SO4)
  7. concentrationAfter concentration
  8. customthe crude product was purified via flash chromatography
  9. washeluting with hexane/acetone (2: 1)

Sources & evidence

ORD record
ord-3415533075b44663a5f7f06a88718314
Source dataset
uspto-grants-1994_03
Patent number
US05298626

Reaction notes

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