1-Bromo-2-Chloroethane → HCID 19705538, compound
Reaction equation
[O:1]=[C:2]1[C:6]([C:15]([CH3:17])=[CH2:16])([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH2:4][N:3]1[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Li+].CC([N-]C(C)C)C.Br[CH2:35][CH2:36][Cl:37]>C1COCC1>[Cl:37][CH2:36][CH2:35][CH:7]([C:6]1([C:15]([CH3:17])=[CH2:16])[CH2:5][CH2:4][N:3]([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:2]1=[O:1])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A cold (-78° C.) solution of tert-butyl 2-oxo-1-(2-phenylethyl)-3-(propen-2-yl)-3-pyrrolidineacetate (prepared similarly to that described in EXAMPLE 1, step 3; 5.52 g, 16.1 mmol) in dry THF (100 mL) is treated with the dropwise addition of LDA (9.66 mL, 19.3 mmol, 2.0N). The solution is stirred for 30 min, and then treated with the dropwise addition of 1-bromo-2-chloroethane (1.61 mL, 19.3 mmol). The solution is maintained at -78° C. for 5 hours and then allowed to slowly warm to room temperature under N2 overnight. The solution is quenched with saturated NH4Cl (10 mL) and diluted with H2O (25 mL). The product is extracted with EtOAc (3×100 mL), dried over anhydrous MgSO4, filtered, and concentrated to give 6.6 g of a brown oil. The oil is purified by silica gel chromatography (275 g SG; 10% EtOAc/hexane) to provide 5.07 g (78%) of the title compound as a clear, yellow oil:
Workup
- temperatureto slowly warm to room temperature under N2 overnight
- customThe solution is quenched with saturated NH4Cl (10 mL)
- additiondiluted with H2O (25 mL)
- extractionThe product is extracted with EtOAc (3×100 mL)
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9f164a419ca84ce9b3014d080076bbec
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05712300
Reaction notes
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