Ethyl bromoacetate → Ethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-1-piperidineacetate

HRID 634615Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][NH:11][C:10]1=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]1=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

(3RS)-3-tert-butoxycarbonylaminopiperidin-2-one (16.07 g) was dissolved in N,N-dimethylformamide (DMF, 350 ml) and the mixture was cooled to 0° C. Sodium hydride (3.6 g of a 50% dispersion in mineral oil) was added and then the mixture was stirred at 0° C. for one hour. A solution of ethyl bromoacetate (13.78 g) in DMF (20 ml) was then added. The mixture was stirred for 16 hours at ambient temperature, then cooled to 0° C. and ice added. Volatile material was removed by evaporation and the residue was partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried over Na2SO4 and concentrated by evaporation. The resulting oil was purified on silica eluting with 40% ethyl acetate/petroleum ether (60-80° C.) to give ethyl 2-[(3RS)-3-tert-butoxycarbonylamino-2-oxopiperidin-1-yl]acetate as a colourless oil (18.15 g).

Workup

stirringThe mixture was stirred for 16 hours at ambient temperature
temperaturecooled to 0° C.
additionice added
customVolatile material was removed by evaporation
customthe residue was partitioned between ethyl acetate and brine
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated by evaporation
customThe resulting oil was purified on silica eluting with 40% ethyl acetate/petroleum ether (60-80° C.)

Sources & evidence

ORD record: ord-553aba9a25e1417bae03224d9fd5b172
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184207B2

Reaction notes

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