HCID 67998996, compound → HCID 68000217, compound

HRID 932079Notes

Reaction equation

HRID 932079 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-0f3fda49b5cc45bb8d975c0382e3cbc7
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

Loading…