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

HRID 868217Notes

Reaction equation

HRID 868217 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]=12

Participants

4

Reactant 2

HCID 27398652,3-dihydro-9-methyl-1H-pyrrolo[1,2-a]indol-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 107739312,3-Dihydro-9-methyl-1H-pyrrolo[1,2-a]indol-1-olYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. customevaporated to near-dryness
  2. extractionThe product was extracted with chloroform (3×75 mL)
  3. dry with materialthe combined organic layer dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-da9452a44ede4d95ad53dce14e93b0e6
Source dataset
uspto-grants-1988_10
Patent number
US04778812

Reaction notes

Loading…