HCID 58109176, compound → HCID 58109640, compound

HRID 2037599Notes

Reaction equation

HRID 2037599 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:23][CH2:24][CH:25]=[O:26])([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.[CH3:28][Mg+].[Br-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)([CH2:23][CH2:24][CH:25]([OH:26])[CH3:28])[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 58109176HCID 58109176, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 58109640HCID 58109640, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanal (300 mg, 0.69 mmol) in THF (4 ml) was added dropwise MeMgBr (0.7 ml, 3 mol/L) at −78° C. The mixture was stirred for 2 h and the temperature was allowed to be warm to rt at this stage. The reaction was quenched with aqueous NH4Cl. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated to give the crude product, which was purified by HPLC and chiral HPLC to give two isomers.

Workup

  1. customThe reaction was quenched with aqueous NH4Cl
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1d89fc6e2b3b402c877fe3fd8de7afd6
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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