Acetone → HCID 59239817, compound

HRID 1668376Notes

Reaction equation

[C:1]([N:4]([CH3:24])[N:5]([C:13]1[CH:18]=[CH:17][C:16]([C:19](OCC)=[O:20])=[CH:15][CH:14]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].[BH4-].[Li+].C(O)C.CC(C)=O>C1COCC1>[C:1]([N:4]([CH3:24])[N:5]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 2-acetyl-1-[4-(ethoxycarbonyl)phenyl]-2-methylhydrazinecarboxylate (2.06 g) was dissolved in THF (60 ml), lithium borohydride (90%, 0.74 g) was added, and ethanol (15 ml) was slowly added dropwise. The obtained mixture was stirred at 80° C. for 3 hr. Acetone (6.0 ml) was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed with water and then saturated brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 (volume ratio)→1:2 (volume ratio)), and further recrystallized from ethyl acetate to give the title compound (1.22 g) as colorless crystals.

Workup

concentrationthe mixture was concentrated under reduced pressure
additionEthyl acetate was added to the residue
washthe mixture was washed with water
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane
customethyl acetate=9:1 (volume ratio)→1:2 (volume ratio)), and further recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-63394e9a6576480c8da30f02be1528da
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989445B2

Reaction notes

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