Allyl bromide → HCID 11109849, compound

HRID 601716Notes

Reaction equation

HRID 601716 reaction equation
[C:1]([N:8]1[C@H:12]([CH3:13])[C@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:10][C:9]1=[O:20])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:31](Br)[CH:32]=[CH2:33]>C1COCC1>[CH2:33]([C@H:2]([CH2:3][CH2:4][CH2:5][CH3:6])[C:1]([N:8]1[C@H:12]([CH3:13])[C@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:10][C:9]1=[O:20])=[O:7])[CH:32]=[CH2:31]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10858719HCID 10858719, compound

Product 1

HCID 11109849HCID 11109849, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of step G (1) (208 mg, 756 μmol) in THF (1.5 mL) at −78° C. was added 1 M NaHMDS (832 μL, 832 μmol) dropwise. After 10 minutes, allyl bromide (196 μL, 2.27 mmol) was added in one shot. The reaction was continued at −78° C. until TLC showed complete reaction (˜6 hours). The reaction was quenched with saturated ammonium chloride solution and allowed to come to room temperature. The mixture extracted 3 times with ethyl acetate. The combined organic layers were dried with MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (0% to 10% EtOAc/Hexane gradient) afforded pure product (137 mg, 58%). 1H NMR (500 MHz, CDCl3) δ ppm 0.93-0.81 (m, 6H) 1.35-1.21 (m, 4H) 1.53-1.44 (m, 1H) 1.75-1.66 (m, 1H) 2.34-2.22 (m, 1H) 2.47-2.36 (m, 1H) 3.98-3.86 (m, 1H) 4.82-4.74 (m, 1H) 5.08-4.94 (m, 2H) 5.63 (d, J=7.32 Hz, 1H) 5.87-5.75 (m, 1H) 7.46-7.24 (m, 5H). HPLC retention time: 1.92 min (method A). MS (ESI) (M+H)+ 316.

Workup

  1. customwas continued at −78° C. until TLC
  2. customreaction (˜6 hours)
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. customto come to room temperature
  5. extractionThe mixture extracted 3 times with ethyl acetate
  6. dry with materialThe combined organic layers were dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6d9026a47d54a4997790fdd5da3c9b6
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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