HCID 67998996, compound → HCID 68000217, compound

HRID 1048392Notes

Reaction equation

HRID 1048392 reaction equation
[CH2:1]([C@@:4]1([CH3:32])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@H:24]([CH2:27][C:28](=[O:30])[CH3:29])[CH2:25][CH3:26])[C:5]1=[O:31])[CH:2]=[CH2:3].[CH3:33][Mg]Br>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([C@@:4]1([CH3:32])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N:6]([C@H:24]([CH2:27][C:28]([OH:30])([CH3:33])[CH3:29])[CH2:25][CH3:26])[C:5]1=[O:31])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 67998996HCID 67998996, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68000217HCID 68000217, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-((S)-5-oxohexan-3-yl)piperidin-2-one (90 mg, 0.19 mmol; Example 131, Step A) in THF (1.9 mL) was added 1.4 M methylmagnesium bromide in toluene and THF (75:25) (408 μL, 0.571 mmol) at 0° C. Then the reaction was allowed to warm to rt and stirred for 4 h. The reaction was quenched (sat NH4Cl solution), extracted (2×EtOAc), and washed (sat. aq. NaCl solution). The combined organic layer was dried (Na2SO4) and concentrated under reduced pressure and purification of the residue by chromatography on silica gel (12 g SiO2, 30% and 35% EtOAc/Hex) provided the title compound as a colorless foam.

Workup

  1. customThe reaction was quenched (sat NH4Cl solution)
  2. extractionextracted (2×EtOAc)
  3. washwashed (sat. aq. NaCl solution)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure and purification of the residue by chromatography on silica gel (12 g SiO2, 30% and 35% EtOAc/Hex)

Sources & evidence

ORD record
ord-89fab8fc8db14d2b81d9ba5cafffe890
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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