Allyl bromide → HCID 86617963, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:15]([N:17]1[CH2:21][CH2:20][C@H:19]([F:22])[CH2:18]1)=[O:16])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[K+].[CH2:33](Br)[CH:34]=[CH2:35]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:10]([CH2:35][CH:34]=[CH2:33])[C:11]([O:13][CH3:14])=[O:12])[C:15]([N:17]1[CH2:21][CH2:20][C@H:19]([F:22])[CH2:18]1)=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of the product from Step A (4.51 g, 14.2 mmol) in THF (150 mL) was added potassium hexamethyldisilazide (65.0 mL, 0.5M in toluene, 32.5.0 mmol) at −78° C. The resulting mixture was stirred at −78° C. for 30 min. Allyl bromide (6.2 mL, 71.7 mmol) was then added. After stirring at −78° C. for 2 h, the reaction was quenched with saturated aqueous ammonium chloride solution. The organic phase was separated and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic layers were washed with brine and concentrated in vacuo. Purification by flash chromatography (30:70 hexanes/ethyl acetate) afforded the desired product (major diastereoisomer from the reaction).
Workup
- stirringAfter stirring at −78° C. for 2 h
- customthe reaction was quenched with saturated aqueous ammonium chloride solution
- customThe organic phase was separated
- extractionthe aqueous phase was extracted with two portions of ethyl acetate
- washThe combined organic layers were washed with brine
- concentrationconcentrated in vacuo
- customPurification by flash chromatography (30:70 hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-86952a3b88fd462f88a0994b070a711b
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687492B2
Reaction notes
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