Sodium borohydride → HCID 14254881, compound

HRID 868216Notes

Reaction equation

HRID 868216 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:18])[CH2:16][N:7]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]([CH3:15])=[C:6]2[C:5]1=[O:17]>CO>[CH3:3][C:4]1([CH3:18])[CH2:16][N:7]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]([CH3:15])=[C:6]2[CH:5]1[OH:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14254880HCID 14254880, compound

Product 1

HCID 14254881HCID 14254881, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Sodium borohydride (1.93 g, 50.7 mmole) was added portionwise upon mild cooling to a solution of 2,3-dihydro-2,2,9-trimethyl-1H-pyrrolo[1,2-a]indol-1-one (3.62 g, 16.9 mmole) in methanol (80 mL). The reaction mixture was stirred at 25° C. overnight. The solvent was removed in vacuo, and the residue was suspended in water (80 mL). The product was extracted with chloroform (3×50 mL). The combined organic layers were washed with brine (50 mL), then dried over MgSO4, filtered, and evaporated to dryness in vacuo to afford 3.49 g (96%) of product, m.p. 82°-85° C., as a light amber solid.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionThe product was extracted with chloroform (3×50 mL)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5220dd5f15d34556a2045a467d949f21
Source dataset
uspto-grants-1988_10
Patent number
US04778812

Reaction notes

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