Ethanol → HCID 67183847, compound

HRID 2425538Notes

Reaction equation

HRID 2425538 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8](=O)[CH3:9])[CH:4]=[N:3]1.[C:11]1([C@H:17]([NH2:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)C.[BH4-].[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C1COCC1>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C@H:8]([NH:19][C@@H:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:18])[CH3:9])[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 702EthanolHCID 6431891-Phenethylamine, (+)-HCID 4311764Sodium borohydrideHCID 70194271-(1,5-dimethyl-1H-pyrazol-4-yl)ethanone

Product 1

HCID 67183847HCID 67183847, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-(1,5-Dimethyl-1H-pyrazol-4-yl)ethanone (J. Heterocyclic Chem. 1986, 23, 275-279, 4.82 g, 34.9 mmol) and (R)-1-Phenylethylamine (5.07 g, 41.9 mmol) in Titanium tetraisopropoxide (22.1 g, 77.7 mmol) were stirred at room temperature for 16 hours. Ethanol (30 ml) and THF (30 ml) were added at −20° C., then Sodium borohydride (3.96 g, 105 mmol) was added at −20° C. then the whole mixture was stirred for 3 h whilst warming to room temperature. The reaction was quenched with water (20 ml) and diluted with ethyl acetate-THF. Then the mixture was filtered through celite and washed with ethyl acetate. The filtrate was dried over Na2SO4, concentrated and purified by silica gel column chromatography eluted with ethyl acetate/n-Hexane=2/1 to 100/0 to furnish the title compound (3.44 g, 41% yield) as colorless oil. 1H NMR (270 MHz, CDCl3) δ 1.26 (3H, d, J=6.6 Hz), 1.27 (3H, d, J=6.6 Hz), 1.96 (3H, s), 3.44 (1H, q, J=6.6 Hz), 3.60 (1H, q, J=6.6 Hz), 3.76 (3H, s), 7.20-7.38 (6H, m).

Workup

  1. customThe reaction was quenched with water (20 ml)
  2. additiondiluted with ethyl acetate-THF
  3. filtrationThen the mixture was filtered through celite
  4. washwashed with ethyl acetate
  5. dry with materialThe filtrate was dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography
  8. washeluted with ethyl acetate/n-Hexane=2/1 to 100/0

Sources & evidence

ORD record
ord-c36e33100e8d4fc5beb228eb453fdb98
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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