Formaldehyde → tert-butyl 1-[2-(4-fluorophenyl)ethyl]-2-methyl-5-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxylate

HRID 1514640Notes

Reaction equation

HRID 1514640 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([CH:23]2[CH2:28][CH2:27][N:26]([C:29](OCC3C=CC=CC=3)=O)[CH2:25][CH2:24]2)[N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C=O.[H][H]>CO.C(O)(=O)C.[Pd]>[F:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][N:11]2[C:10]([CH:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=[CH:9][C:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[C:12]2[CH3:13])=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 66670197benzyl 4-{4-(tert-butoxycarbonyl)-1-[2-(4-fluorophenyl)ethyl]-5-methyl-1H-pyrrol-2-yl}piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 66670175tert-butyl 1-[2-(4-fluorophenyl)ethyl]-2-methyl-5-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 340 mg portion of benzyl 4-{4-(tert-butoxycarbonyl)-1-[2-(4-fluorophenyl)ethyl]-5-methyl-1H-pyrrol-2-yl}piperidine-1-carboxylate was dissolved in 7 ml of methanol, and 159 μl of 37% formalin, 3 drops of acetic acid and 45 mg of 10% palladium-activated carbon were added, followed by stirring at room temperature for 2 hours in an atmosphere of hydrogen. The reaction liquid was filtered through celite, the filtrate was concentrated under a reduced pressure, 50 ml of a saturated sodium bicarbonate aqueous solution was added to the residue, and the resulting solid was collected by filtration to obtain 232 mg of tert-butyl 1-[2-(4-fluorophenyl)ethyl]-2-methyl-5-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxylate as a colorless solid.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through celite
  3. concentrationthe filtrate was concentrated under a reduced pressure, 50 ml of a saturated sodium bicarbonate aqueous solution
  4. additionwas added to the residue
  5. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-c13ec720f4bc4c579080d45735ca7303
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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