HCID 86744587, compound → HCID 86744586, compound

HRID 981318Notes

Reaction equation

HRID 981318 reaction equation
[OH:1][C@H:2]1[C@H:7]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16]CC2C=CC=CC=2)[CH2:6][CH2:5][N:4]([CH:25]([CH3:45])[CH2:26][C:27]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:28]([N:30]([CH3:32])[CH3:31])=[O:29])[CH2:3]1.[H][H]>[Pd].CO>[OH:1][C@H:2]1[C@H:7]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH2:6][CH2:5][N:4]([CH:25]([CH3:45])[CH2:26][C:27]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:28]([N:30]([CH3:31])[CH3:32])=[O:29])[CH2:3]1

Participants

5

Reactant 2

HCID 86744587HCID 86744587, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86744586HCID 86744586, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.7 parts of trans-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-4-[[2-(phenylmethoxy)benzoyl]amino]-1-piperidinebutanamide and 120 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was taken up in methylbenzene and the solvent was evaporated again. The residue was suspended in a mixture of 2,2'-oxybispropane and a few drops of acetonitrile. The product was filtered off and dried in vacuo at 70° C., yielding 1.3 parts (63.0%) of trans-3-hydroxy-4-[(2-hydroxybenzoyl)-amino]-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide; mp. 154.3° C. (compound 77).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customthe solvent was evaporated again
  8. additionThe residue was suspended in a mixture of 2,2'-oxybispropane and a few drops of acetonitrile
  9. filtrationThe product was filtered off
  10. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-6b5304b05d38423cbee66643cdcbffd0
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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