(S)-1-(1-(4-bromophenyl)ethylamino)-4-methylpentan-3-one → 1-((S)-1-(4-bromophenyl)ethylamino)-3-isopropylhex-5-en-3-ol

HRID 470542Notes

Reaction equation

HRID 470542 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])[CH3:9])=[CH:4][CH:3]=1.[CH2:18]([Mg]Br)[CH:19]=[CH2:20]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13]([CH:14]([CH3:16])[CH3:15])([OH:17])[CH2:20][CH:19]=[CH2:18])[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 59635646(S)-1-(1-(4-bromophenyl)ethylamino)-4-methylpentan-3-oneHCID 178455850HCID 178455850, compound

Product 1

HCID 596357281-((S)-1-(4-bromophenyl)ethylamino)-3-isopropylhex-5-en-3-olYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (S)-1-(1-(4-bromophenyl)ethylamino)-4-methylpentan-3-one (740 mg, 2.5 mmol) in THF (25 mL) was added dropwise allylmagnesium bromide (25 mL, 25 mmol) under N2 at −78° C. The reaction mixture was stirred at −78° C. for 2 h, quenched by addition of satd aq NH4Cl, and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and filtered. The solvent was removed under vacuo to give 1-((S)-1-(4-bromophenyl)ethylamino)-3-isopropylhex-5-en-3-ol (802 mg, 95% yield), which was used directly in the next step.

Workup

  1. customquenched by addition of satd aq NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed under vacuo

Sources & evidence

ORD record
ord-fea24990f8664cb0bb7ad1b4c81c3f44
Source dataset
uspto-grants-2014_01
Patent number
US08629138B2

Reaction notes

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