Hydrochloric Acid → 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxo-1-(pentan-3-yl)piperidin-3-yl)acetic acid

HRID 931970ノート

反応式

HRID 931970 の反応式
[CH2:1]([C@@:4]1(C)[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]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:5]1=[O:29])C=C.C(Cl)(Cl)(Cl)Cl.I([O-])(=O)(=O)=O.[Na+].Cl.CC[O:45][C:46]([CH3:48])=[O:47]>C(#N)C.O.[Ru](Cl)(Cl)Cl.O>[Cl:16][C:12]1[CH:11]=[C:10]([C@@H:8]2[C@@H:7]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:6]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:5](=[O:29])[C@:4]([CH2:48][C:46]([OH:45])=[O:47])([CH3:1])[CH2:9]2)[CH:15]=[CH:14][CH:13]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 5943Carbon TetrachlorideHCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 58573148(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-(pentan-3-yl)piperidin-2-one

生成物 1

HCID 565911372-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxo-1-(pentan-3-yl)piperidin-3-yl)acetic acid

試薬・触媒・溶媒 3

HCID 6093376Ruthenium trichloride hydrate触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 725 mg (1.63 mmol) of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-(pentan-3-yl)piperidin-2-one (Example 3, Step A) in a mixture of acetonitrile (4 mL), carbon tetrachloride (4 mL) and water (5.9 mL) added 1.40 g (6.53 mmol) of sodium periodate followed by 44 mg (0.20 mmol) of ruthenium(III) chloride hydrate. The dark brown biphasic mixture was stirred vigorously at room temperature for 21 h, and then was acidified with 1 N HCl. The mixture was diluted with EtOAc and filtered through a pad of Celite® (J. T. Baker, Phillipsberg, N.J., diatomaceous earth). After filtration, the layers were separated and the aqueous layer was extracted with EtOAc (1×). The combined organic layers were washed with saturated aqueous sodium chloride (1×), then were dried over Na2SO4, filtered and the filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (0 to 25% MeOH/DCM, gradient elution) provided the title compound as a white solid.

後処理

  1. filtrationfiltered through a pad of Celite® (J. T. Baker, Phillipsberg, N.J., diatomaceous earth)
  2. filtrationAfter filtration
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (1×)
  5. washThe combined organic layers were washed with saturated aqueous sodium chloride (1×)
  6. dry with materialwere dried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customPurification of the residue by flash chromatography on silica gel (0 to 25% MeOH/DCM, gradient elution)

出典と根拠

ORDレコード
ord-474c459ed4df45ba831f0d0be0c96a0c
出典データセット
uspto-grants-2016_03
特許番号
US09296736B2

反応ノート

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