HCID 58109676, compound → HCID 58109274, compound

HRID 2037447Notes

Reaction equation

HRID 2037447 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][CH:31]=[O:32])([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:33])[CH3:16])=[CH:11][CH:10]=1.[CH3:34][Mg+].[Br-]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@@:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)([CH2:30][CH:31]([OH:32])[CH3:34])[O:19][C:18]2=[O:33])[CH3:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 58109676HCID 58109676, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 58109274HCID 58109274, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-((S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)acetaldehyde in THF (3 mL) was added MeMgBr (1.4 M in toluene/THF, 3 mL, 4.2 mmol) at 0° C. The mixture was warmed up to rt and stirred for 1.5 h before quenching with satd aq NH4Cl (3 mL). The mixture was diluted with CH2Cl2 and dried over Na2SO4. Removal of the solvent gave the crude alcohol as a mixture of diastereomers.

Workup

  1. custombefore quenching with satd aq NH4Cl (3 mL)
  2. additionThe mixture was diluted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-d4bdd9b855084474b9a29da8fbc2b152
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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