Ethyl bromoacetate → HCID 25175166, compound
Reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([C:18]2[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=2)[CH2:13]1.[H-].[Na+].Br[CH2:28][C:29]([O:31]CC)=[O:30].CC(C)([O-])C.[K+]>CN(C=O)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([C:18]2[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=2)[O:24][CH2:28][C:29]([OH:31])=[O:30])[CH2:13]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (R*)-3-{1-[(S)-1-(2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl]piperidin-3-yl}phenol (201 mg, 0.62 mmol) in dry DMF (2 ml) was added NaH (60% in oil, 30 mg, 0.75 mmol) under nitrogen atmosphere and the mixture was stirred at 0° C. for 5 min, then allowed to warm to RT and stirred for further 2.5 h. The reaction mixture was cooled to 0° C., ethyl bromoacetate (106 mg, 0.62 mmol) was added and the mixture was stirred at RT overnight. Potassium tert-butoxide (69 mg, 0.61 mmol) was added and the mixture was stirred for 3 h at RT and filtered. The precipitate was dissolved in dry MeOH, the solution filtered and evaporated to dryness to give 170 mg of the title compound.
Workup
- temperatureto warm to RT
- stirringstirred for further 2.5 h
- temperatureThe reaction mixture was cooled to 0° C.
- stirringthe mixture was stirred at RT overnight
- stirringthe mixture was stirred for 3 h at RT
- filtrationfiltered
- dissolutionThe precipitate was dissolved in dry MeOH
- filtrationthe solution filtered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-8fd8156a901042cc8cdeb8718fe1d523
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492549B2
Reaction notes
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