HCID 13362828, compound → HCID 18919524, compound

HRID 1290882Notes

Reaction equation

HRID 1290882 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][C:29](=[O:31])[CH3:30])[CH2:22][CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH:7]([N:20]1[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][CH:29]([OH:31])[CH3:30])[CH2:24][CH2:25]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 13362828HCID 13362828, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18919524HCID 18919524, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Lithium aluminium hydride (97 mg, 2.56 mmol) was taken up in dry THF (15 ml) and stirred under an inert atmosphere at -78° C. 5-(4-Benzhydrylpiperazin-1-yl)-2-pentanone (717 mg, 2.13 mmol) as a solution in THF (35 ml) was added dropwise. The reaction was stirred at -78° C. for 15 minutes before allowing to warm to room temperature. After a total reaction time of 30 minutes the reaction was quenched with a 15% aqueous solution of sodium hydroxide (25 ml). The reaction mixture was filtered through Kieselguhr gel and partitioned between ethyl acetate and water. The organic layer was separated, dried over sodium sulphate, filtered and solvent removed under reduced pressure to yield (RS)-5-(4-benzhydrylpiperazin-1-yl)-2-pentanol as a white powder (686 mg, 95%).

Workup

  1. stirringThe reaction was stirred at -78° C. for 15 minutes
  2. temperatureto warm to room temperature
  3. customAfter a total reaction time of 30 minutes the reaction was quenched with a 15% aqueous solution of sodium hydroxide (25 ml)
  4. filtrationThe reaction mixture was filtered through Kieselguhr gel
  5. custompartitioned between ethyl acetate and water
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-923400eaaee94316906efeafbbf1c399
Source dataset
uspto-grants-1998_05
Patent number
US05753671

Reaction notes

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