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

HRID 1191864Notes

Reaction equation

HRID 1191864 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-06f5d7dcb8e24f1f9ff976b7f19d0cd2
Source dataset
uspto-grants-2014_03
Patent number
US08680093B2

Reaction notes

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