Sodium borohydride → HCID 22458855, compound

HRID 2184933Notes

Reaction equation

HRID 2184933 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:17](=[O:19])[CH3:18])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([CH:20]=[O:21])[CH:8]=2)[CH3:2].[BH4-].[Na+]>CCO>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:17](=[O:19])[CH3:18])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([CH2:20][OH:21])[CH:8]=2)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22458811HCID 22458811, compound

Product 1

HCID 22458855HCID 22458855, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(9-Ethyl-6-formyl-9H-carbazol-3-yl)-acetamide (50 mg, 0.150 mmol) in EtOH (5 ml) at 0° C. was added NaBH4 (8.5 mg, 0.225 mmol), and after 10 minutes the cooling bath was removed. After 1 hour additional NaBH4 (2 mg) was added, and after stirring 90 minutes water was added, the EtOH removed in vacuo, and the aqueous layer extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated to afford the crude product. Chromatographic purification (silica, 50% EtOAc/Hex) afforded the product as a solid (28 mg, 56% yield). MS m/z @ 337 (m+1).

Workup

  1. customafter 10 minutes the cooling bath was removed
  2. additionAfter 1 hour additional NaBH4 (2 mg) was added
  3. additionwas added
  4. customthe EtOH removed in vacuo
  5. extractionthe aqueous layer extracted with CH2Cl2
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated
  8. customto afford the crude product
  9. customChromatographic purification (silica, 50% EtOAc/Hex)

Sources & evidence

ORD record
ord-dbb9095b484f4e7d88e6888690f29c73
Source dataset
uspto-grants-2002_06
Patent number
US06399631B1

Reaction notes

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