Water → HCID 86729766, compound

HRID 2272609Notes

Reaction equation

HRID 2272609 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:17](=[O:25])[CH2:18][CH:19]([CH3:24])[CH2:20][C:21](O)=[O:22])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].O>C1COCC1>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:17](=[O:25])[CH2:18][CH:19]([CH3:24])[CH2:20][CH2:21][OH:22])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 4649610HCID 4649610, compound

Product 1

HCID 86729766HCID 86729766, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the compound obtained in Step 1 (1.0 g, 2.96 mmol) in THF (10 mL) was added a THF (5.91 mL, 5.91 mmol) solution of 1M borane-tetrahydrofuran complex at room temperature, and the mixture was stirred for 14 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give N-(9-ethyl-9H-carbazol-3-yl)-5-hydroxy-3-methylpentanamide (0.514 g, 1.586 mmol, 53.7%) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9ba588565e99447db45e1dcde1d4922d
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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