(5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(dicyclopropylmethyl)-5,6-dihydropyridin-2(1H)-one → (5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(dicyclopropylmethyl)piperidin-2-one

HRID 1048347Notes

Reaction equation

HRID 1048347 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([CH:21]([CH:25]3[CH2:27][CH2:26]3)[CH:22]3[CH2:24][CH2:23]3)[C:11](=[O:28])[CH:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[H][H]>C(Cl)Cl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CC=CCCC=C1.C1C=CN=CC=1.F[P-](F)(F)(F)(F)F.[Ir]>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)[N:12]([CH:21]([CH:22]3[CH2:24][CH2:23]3)[CH:25]3[CH2:27][CH2:26]3)[C:11](=[O:28])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67998565(5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(dicyclopropylmethyl)-5,6-dihydropyridin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 68000998(5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(dicyclopropylmethyl)piperidin-2-one

Reagents, catalysts & solvents 2

HCID 5702647(1,5-Cyclooctadiene)pyridine(tricyclohexylphosphine)iridium hexafluorophosphateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A solution of (5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(dicyclopropylmethyl)-5,6-dihydropyridin-2(1H)-one (Example 115, Step H, 0.826 g, 2.003 mmol) and (1,5-cyclooctadiene)(pyridine) (tricyclohexylphosphine)iridium (i) hexafluorophosphate (0.129 g, 0.160 mmol) in DCM (60.0 ml) was saturated with hydrogen. The resulting mixture was stirred at rt under a hydrogen atmosphere for 2 h, then another 66.0 mg of (1,5-cyclooctadiene)(pyridine) (tricyclohexylphosphine)iridium (i) hexafluorophosphate were added. Stirring under hydrogen atmosphere was continued until LCMS indicated complete saturation of the double bond. The solvent was removed and the crude mixture was purified by chromatography on silica gel (eluting with ethyl acetate:hexane, 10:90) to give the title compound.

Workup

  1. stirringStirring under hydrogen atmosphere
  2. customThe solvent was removed
  3. customthe crude mixture was purified by chromatography on silica gel (eluting with ethyl acetate:hexane, 10:90)

Sources & evidence

ORD record
ord-a6681dda6bf041a198edc5598a3bc3ad
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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