2,3-dihydro-9-methyl-1H-pyrrolo[1,2-a]indol-1-one → 2,3-Dihydro-9-methyl-1H-pyrrolo[1,2-a]indol-1-ol
Reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]2[CH2:13][CH2:14][C:15](=[O:16])[C:5]=12>CO>[CH3:3][C:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]2[CH2:13][CH2:14][CH:15]([OH:16])[C:5]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Sodium borohydride (1.368 g, 36 mmole) was added portionwise to a solution of 2,3-dihydro-9-methyl-1H-pyrrolo[1,2-a]indol-1-one, prepared by the process of Example 1, Step 1, (2.22 g, 12 mmole) in methanol (200 mL). The reaction mixture was stirred at 25° C. for 2 hours, evaporated to near-dryness, and the residue suspended in water (150 mL). The product was extracted with chloroform (3×75 mL), and the combined organic layer dried over MgSO4, filtered, and evaporated to dryness. The residue was crystallized from ether to afford 1.32 g (59%) of product, m.p. 118.5°-120° C., as an off-white solid.