Thiophene → Ethyl trans-3-hydroxy-4-[methyl(phenylmethyl)amino]-1-piperidinecarboxylate

HRID 981300Notes

Reaction equation

HRID 981300 reaction equation
[OH:1][C@H:2]1[C@H:7]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5][N:4]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:3]1.S1C=CC=[CH:22]1.[H][H]>CO.[Pd]>[OH:1][C@H:2]1[C@H:7]([N:8]([CH3:22])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5][N:4]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:3]1

Participants

7

Reactant 4

HCID 8030ThiopheneHCID 13677850Ethyl trans-3-hydroxy-4-[(phenylmethyl)amino]-1-piperidinecarboxylateHCID 178418361HCID 178418361, compoundHCID 178486302HCID 178486302, compound

Product 1

HCID 67928745Ethyl trans-3-hydroxy-4-[methyl(phenylmethyl)amino]-1-piperidinecarboxylateYield 79.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

(a-2) A mixture of 40 parts of ethyl trans-3-hydroxy-4-[(phenylmethyl)-amino]-1-piperidinecarboxylate, 15 parts of poly(oxymethylene), 2 parts of a solution of thiophene in methanol and 400 parts of methanol was hydrogenated at normal pressure and at room temperature with 4 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 dissolved in trichloromethane. The organic layer was washed successively with a dilute ammonium hydroxide solution and water, dried, filtered and evaporated in vacuo. The residue was crystallized from 80 parts of acetonitrile The product was filtered off and dried, yielding 32.7 parts (79.9%) of ethyl trans-3-hydroxy-4-[methyl(phenylmethyl)amino]-1-piperidinecarboxylate (interm. 6).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in trichloromethane
  4. washThe organic layer was washed successively with a dilute ammonium hydroxide solution and water
  5. customdried
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was crystallized from 80 parts of acetonitrile The product
  9. filtrationwas filtered off
  10. customdried

Sources & evidence

ORD record
ord-1c974843383849e2b1c7b21b0f604ab4
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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