Ammonium formate → HCID 19710232, compound

HRID 725925Notes

Reaction equation

HRID 725925 reaction equation
[CH2:1]([N:8](CCC)[CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][C:13]([N:18]3[CH:22]=[CH:21][CH:20]=[CH:19]3)=[CH:14][CH:15]=2)[CH2:10]1)[C:2]1C=CC=C[CH:3]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:1]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][C:13]([N:18]3[CH:22]=[CH:21][CH:20]=[CH:19]3)=[CH:14][CH:15]=2)[CH2:10]1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 19710213HCID 19710213, compound

Product 1

HCID 19710232HCID 19710232, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl-propyl-(6-pyrrol-1-yl-indan-2-yl)-amine (540 mg, 1.64 mmol), ammonium formate (0.8 g, 12.6 mmol) and 10% Pd/C (0.3 g) in 99% ethanol (50 mL) was stirred for at ambient temperature for 1 h. The mixture was filtered on a Celite pad and the solution concentrated in vacuo. The residue was redissolved in 10% sodium carbonate/diethyl ether. After 2 additional ether extractions of the aqueous phase, the combined ethereal phases were dried (magnesium sulfate) filtered and evaporated to yield 320 mg of a residue containing both the pyrrolo and the pyrrolidino derivative. The two compounds were separated on a silica column using methanol as eluant, yielding 230 mg (58%) of the pyrrolo derivative and 40 mg (10%) of the pyrrolidino derivative.: 1H NMR (300 MHz, CDCl3) δ 0.93 (t, 3H), 1.52 (m, 2H), 2.61 (t, 2H), 2.77 (m, 2H), 3.18 (m, 2H), 3.67 (m, 1H), 6.31 (m, 2H), 7.03 (m, 2H), 7.1-7.3 (m, 3H); MS m/e 240 (M+, 72), 211 (100), 182 (72), 171 (65), 115 (25).

Workup

  1. filtrationThe mixture was filtered on a Celite pad
  2. concentrationthe solution concentrated in vacuo
  3. dissolutionThe residue was redissolved in 10% sodium carbonate/diethyl ether
  4. extractionAfter 2 additional ether extractions of the aqueous phase
  5. dry with materialthe combined ethereal phases were dried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-304ae0101e4b4eaca73e6bc359802e54
Source dataset
uspto-grants-1998_01
Patent number
US05708018

Reaction notes

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