Aluminium lithium hydride → HCID 23627270, compound

HRID 1423103Notes

Reaction equation

HRID 1423103 reaction equation
[CH2:1]([C@H:8]1[NH:13][C:12](=O)[CH2:11][N:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([C@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:16]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23627268HCID 23627268, compound

Product 1

HCID 23627270HCID 23627270, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(R)-6-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-2-one (365 mg, 0.96 mmol) was dissolved in THF (10 mL), cooled to 0° C., and treated with solid lithium aluminum hydride (73 mg, 1.92 mmol). The reaction mixture was heated at 60° C. for 3 hr then cooled to 0° C. and quenched with EtOAc (2 mL) and a 1 N aqueous solution of NaOH (2 mL). The reaction was filtered with the aid of EtOAc, dried over MgSO4, filtered, and evaporated to an oil, which was purified by silica gel flash chromatography with 5% MeOH/CH2Cl2 as eluant to afford the title compound as a brown oil (228 mg, 65%). LC/MS (Method A) 5.12 min, [M+1]+ 367.

Workup

  1. temperatureThe reaction mixture was heated at 60° C. for 3 hr
  2. temperaturethen cooled to 0° C.
  3. customquenched with EtOAc (2 mL)
  4. filtrationThe reaction was filtered with the aid of EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to an oil, which
  8. customwas purified by silica gel flash chromatography with 5% MeOH/CH2Cl2 as eluant

Sources & evidence

ORD record
ord-3dbb19a497e3417b9a9b64ecd42a2334
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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