(S)-2-((3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanal → HCID 58573334, compound

HRID 1048589Notes

Reaction equation

HRID 1048589 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH2:6]([C@@:9]1([CH3:35])[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[C@@H:12]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:11]([C@@H:29]([CH2:32][CH3:33])[CH:30]=[O:31])[C:10]1=[O:34])[CH:7]=[CH2:8]>C1COCC1>[CH2:6]([C@@:9]1([CH3:35])[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[C@@H:12]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[N:11]([C@@H:29]([CH2:32][CH3:33])[CH:30]([CH:1]2[CH2:3][CH2:2]2)[OH:31])[C:10]1=[O:34])[CH:7]=[CH2:8]

Participants

4

Reactant 2

HCID 58573909(S)-2-((3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanalHCID 178418630HCID 178418630, compound

Product 1

HCID 58573334HCID 58573334, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopropylmagnesium bromide (0.5 M solution in THF, 2.0 mL, 1.013 mmol) was added dropwise via syringe over a period of 1 min to a stirred solution of (S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanal (Example 91, Step C, 150 mg, 0.338 mmol) in THF (1.7 mL) at rt. The reaction mixture was stirred at rt for 20 minutes and then quenched with NH4Cl (30 mL, saturated aqueous solution) and diluted with EtOAc (50 mL). The organic layer was dried over MgSO4, filtered and evaporated in vacuo. Purification by column chromatography (24 g SiO2, Hexanes:EtOAc, 1:0 to 4:1) gave the title compound as a mixture of diastereomers.

Workup

  1. customquenched with NH4Cl (30 mL, saturated aqueous solution)
  2. additiondiluted with EtOAc (50 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by column chromatography (24 g SiO2, Hexanes:EtOAc, 1:0 to 4:1)

Sources & evidence

ORD record
ord-c424d5df63294f48a355b135a7945fa0
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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