HCID 18703424, compound → HCID 54376746, compound

HRID 1296314Notes

Reaction equation

HRID 1296314 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12](=O)[NH:11][CH:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 18703424HCID 18703424, compound

Product 1

HCID 54376746HCID 54376746, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226445Aluminium lithium hydrideSolvent

Procedure

To a stirred solution of 1-benzyl-3-(4-trifluoromethyl-benzyl)-piperazine-2,5-dione (0.53 g, 1.46 mmol) in dry THF (15 mL), 1M LAH in THF (6.14 mL, Aldrich) was slowly added at 0° C. and then heated to reflux for 18 h under argon. The reaction was cooled to room temperature and carefully quenched with H2O (1 mL), 1N NaOH (1 mL) and H2O (1 mL). The reaction mixture was filtered through bed of celite and rinsed with THF (100 mL). The filtrate was conc in vacuo and then dissolved in EtOAc (100 mL), washed with brine (2×10 mL), dried over MgSO4, and conc in vacuo to yield 0.45 g (92%) of the product as a colorless oil. MS (ESI) 335 (M+H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 h under argon
  3. customcarefully quenched with H2O (1 mL), 1N NaOH (1 mL) and H2O (1 mL)
  4. filtrationThe reaction mixture was filtered through bed of celite and
  5. washrinsed with THF (100 mL)
  6. dissolutiondissolved in EtOAc (100 mL)
  7. washwashed with brine (2×10 mL)
  8. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-44816b7f461f4fcc8ddd6e50746005d6
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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