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

HRID 634615ノート

反応式

HRID 634615 の反応式
[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]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 21260262tert-Butyl (2-oxopiperidin-3-yl)carbamate

生成物 1

HCID 21260261Ethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-1-piperidineacetate収率 80.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

(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).

後処理

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

出典と根拠

ORDレコード
ord-553aba9a25e1417bae03224d9fd5b172
出典データセット
uspto-grants-2001_02
特許番号
US06184207B2

反応ノート

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