Allyl bromide → HCID 86622345, compound

HRID 501721Notes

Reaction equation

HRID 501721 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C@H:6]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:7][OH:8])=[O:4].[H-].[Na+].Br[CH2:18][CH:19]=[CH2:20]>C1COCC1>[CH2:20]([O:8][CH2:7][C@H:6]([NH:5][C:3](=[O:4])[C:2]([F:13])([F:14])[F:1])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 86622344HCID 86622344, compound

Product 1

HCID 86622345HCID 86622345, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step AK (2): (R)-2,2,2-trifluoro-N-(1-hydroxy-4-methylpentan-2-yl)-acetamide (200 mg, 0.94 mmol) was dissolved in THF (5 mL) under nitrogen atmosphere. Sodium hydride (80 mg, 1.9 mmol) was added to the reaction mixture in portions. 3-Bromoprop-1-ene (0.16 mL, 1.9 mmol) was added dropwise to the reaction mixture. The reaction mixture was stirred at rt for 3 h and was extracted with EtOAc. The combined organic phases were washed with water and brine and dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography to give (R)-N-(1-(allyloxy)-4-methylpentan-2-yl)-2,2,2-trifluoroacetamide (210 mg, 88%) as a colorless oil. LC-MS (M+H)+=254.06. 1H NMR (CD3OD, 500 MHz) δ 5.91 (m, 1H) 5.31-5.17 (m, 2H) 4.21 (m, 1H) 4.05-3.97 (m, 2H) 3.49-3.42 (m, 2H) 1.63 (m, 1H) 1.52 (m, 1H) 1.39 (m, 1H) 0.97-0.93 (m, 6H).

Workup

  1. extractionwas extracted with EtOAc
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9aa37f2b52364012b42b86120f33c2e5
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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