Acetic Acid → 3-[3-Methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-propionaldehyde

HRID 1096254Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].CON(C)[C:10](=[O:32])[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=2)[CH:15]([CH3:30])[C:14]1=[O:31].CC(C)=O.CC(O)=O>C1COCC1>[CH3:30][CH:15]1[N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=2)[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH:10]=[O:32])[C:14]1=[O:31]

Participants

Conditions

Temperature: -75 °C

Procedure

Lithium aluminum hydride solution (1 M in THF (0.46 mL, 0.46 mmol) was added dropwise at −30° C. to a solution of N-methoxy-N-methyl-3-[3-methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-propionamide (180 mg, 0.46 mmol) in THF (10 mL). The reaction mixture was cooled to −75° C., then acetone (0.59 g, 10 mmol) and AcOH (44 mg, 0.93 mmol) were added dropwise. The reaction mixture was then partitioned between TBME and 1 M aq. KHSO4 solution. The organic layer was dried (MgSO4), filtered, and evaporated to afford the title compound (122 mg, 80%). Light yellow oil, MS: 331.1 (M+H)+.

Workup

customThe reaction mixture was then partitioned between TBME and 1 M aq. KHSO4 solution
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-78b0ffe61b8a4a5e9faf065a96a35023
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138175B2

Reaction notes

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