Ethyl Acetate → Ethyl 2-(2-oxo-5-phenyl-1-piperidinyl)butanoate

HRID 7399

Reaction equation

CC(C)([O-])C.[K+].[C:7]1([CH:13]2[CH2:18][NH:17][C:16](=[O:19])[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH:21]([CH2:27][CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(OCC)(=O)C>C1(C)C=CC=CC=1>[O:19]=[C:16]1[CH2:15][CH2:14][CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:18][N:17]1[CH:21]([CH2:27][CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

Conditions

Temperature: 70 °C

Procedure

In a 1 l three necked flask fitted with reflux condenser, magnetic stirrer and dropping funnel under inert atmosphere, 9.8 g (87 mmoles) of potassium t-butoxide were suspended in 600 ml of dry toluene. 11.8 g (67 mmoles) of 5-phenyl-2-piperidinone 25 were added, and the mixture stirred for 30 min. 17 g (87 mmoles) of ethyl 2-bromobutanoate were added and the temperature raised to 70° C. for 5 hours. 600 ml of ethyl acetate were added, the solution was washed twice with brine, the organic phase dried over magnesium sulfate, filtered and concentrated to dryness. The residue was purified by PrepLC (1 kg SiO2, CH2Cl2/EtOH, 97.5/2.5) to give 3.7 g of pure ester 26 as a mixture of diastereomers, 70.4% yield.

Workup

temperaturewith reflux condenser, magnetic stirrer
washthe solution was washed twice with brine
dry with materialthe organic phase dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated to dryness
customThe residue was purified by PrepLC (1 kg SiO2, CH2Cl2/EtOH, 97.5/2.5)

Sources & evidence

ORD record: ord-1eef3dbcfb0c48a58fb44f859aa4293d
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087596B2

Linked notes

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