Lithium diisopropylamide → HCID 68469023, compound
Reaction equation
[C:1]([N:7]1[C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C:8]1=[O:24])(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].[Li+].CC([N-]C(C)C)C.Br[CH2:34][C:35]1[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=1[Cl:42]>C1COCC1>[Cl:42][C:36]1[CH:37]=[CH:38][CH:39]=[C:40]([F:41])[C:35]=1[CH2:34][C@@H:2]([CH2:3][CH:4]=[CH2:5])[C:1]([N:7]1[C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C:8]1=[O:24])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Dissolve (4S,5R)-3-pent-4-enoyl-4,5-diphenyloxazolidin-2-one (1.0 g, 3.1 mmol) in THF (50 mL) and cool the mixture to −78° C. under N2 with stirring. Add dropwise LDA (2.7 mL, 4.0 mmol, 1.5 M in THF) and stir the mixture for 0.5 hours. Then add 2-(bromomethyl)-1-chloro-3-fluorobenzene (1.39 g, 6.22 mmol). Continue to stir the reaction mixture for one hour until TLC shows that the starting material has been consumed. Add water (50 mL) and extract the aqueous with CH2Cl2 (3×250 mL). Combine the organic layers and dry over Na2SO4. Concentrate and purify by chromatography (Silica gel) to afford (4S,5R)-3-((R)-2-(2-Chloro-6-fluorobenzyl)pent-4-enoyl)-4,5-diphenyloxazolidin-2-one (1.44 g, 75.5%).
Workup
- stirringstir the mixture for 0.5 hours
- stirringContinue to stir the reaction mixture for one hour until TLC
- customhas been consumed
- extractionAdd water (50 mL) and extract the aqueous with CH2Cl2 (3×250 mL)
- dry with materialCombine the organic layers and dry over Na2SO4
- concentrationConcentrate
- custompurify by chromatography (Silica gel)
Sources & evidence
- ORD record
- ord-23f4936e01c345c0abc5a5d3f2123aea
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07713979B2
Reaction notes
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