Acetonitrile → HCID 19003058, compound

HRID 1613465Notes

Reaction equation

HRID 1613465 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.Cl.[C:17]1(NC2CC2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([N:29]([CH2:32][CH3:33])CC)C.[C:34](#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:29][CH:32]3[CH2:33][CH:34]3[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:6]1=2

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 15818737HCID 15818737, compoundHCID 44717153HCID 44717153, compound

Product 1

HCID 19003058HCID 19003058, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

To a stirred suspension of 1,4-dihydro-7-hydroxy-4-methylcyclopent[b]indol-3(2H)-one (5.0 g) in acetonitrile (100 ml) was added phenylcyclopropylamine hydrochloride (4.2 g) followed by triethylamine (2.5 g). The solution was stirred at room temperature under a nitrogen atmosphere while titanium (IV) isopropoxide was added in a dropwise manner. The mixture was stirred for 3 hours and thereafter quenched 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-phenylcyclopropyl)imino]-1,2,3,4-tetrahydrocyclopent[b]indol-7-ol.

Workup

  1. additionwas added in a dropwise manner
  2. customquenched 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-a5a1c2d683ea47d48f6e63e564b1dcb1
Source dataset
uspto-grants-1993_03
Patent number
US05192789

Reaction notes

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