Ethyl bromoacetate → HCID 67359342, compound

HRID 2408825Notes

Reaction equation

HRID 2408825 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][CH2:10][NH:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>O1CCCC1>[O:13]=[C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:12][CH2:11][CH2:10][N:9]1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 3211653,3-Diphenyl-3,4,5,6-tetrahydropyridin-2-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 67359342HCID 67359342, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product of Example 1C (2.51 g, 10.00 mmol) in tetrahydrofuran (100 mL) was added potassium tert-butoxide (1.35 g, 12.00 mmol) under nitrogen followed by ethyl 2-bromoacetate (1.22 mL, 11.00 mmol). The reaction mixture was heated to 80° C. and stirred overnight. The reaction mixture was cooled to room temperature, concentrated and then diluted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (20:80) gave the title compound. MS (DCI+) m/z 338 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washSilica gel chromatography eluting with ethyl acetate/hexane (20:80)

Sources & evidence

ORD record
ord-c6e3b4b0a5b84eab904c8fb4a451cc58
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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