Trifluoroacetic acid → HCID 54548736, compound

HRID 2287835Notes

Reaction equation

HRID 2287835 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]([NH:18][CH2:19][C:20]1[N:25]=[CH:24][C:23]2[CH2:26][CH:27]([NH:29]C(=O)OC(C)(C)C)[CH2:28][C:22]=2[CH:21]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[NH2:29][CH:27]1[CH2:26][C:23]2[CH:24]=[N:25][C:20]([CH2:19][NH:18][C:16](=[O:17])[O:15][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:21][C:22]=2[CH2:28]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54568579HCID 54568579, compound

Product 1

HCID 54548736HCID 54548736, compound

Procedure

Trifluoroacetic acid (25 ml) was added to t-butyl [6,7-dihydro-3-[[benzyloxycarbonyl]aminomethyl]-5H-cyclopenta[c]pyridin-6-yl]carbamate (55, 4.45 g, 11.2 mmol) at room temperature, and the mixture was stirred for 20 minutes. Excess trifluoroacetic acid was removed under vacuum, and the residue was partitioned between 1:1 tetrahydrofuran/diethylether and 5% sodium hydroxide solution. The aqueous solution was extracted twice more with 1:1 tetrahydrofuran/diethylether, and the combined extracts were washed with brine and dried (Na2SO4). The solvent was removed under vacuum to leave phenylmethyl [[6-amino-6,7-dihydro-5H-cyclopenta[c]pyridin-3-yl]methyl]carbamate as an amber oil.

Workup

  1. customExcess trifluoroacetic acid was removed under vacuum
  2. customthe residue was partitioned between 1:1 tetrahydrofuran/diethylether and 5% sodium hydroxide solution
  3. extractionThe aqueous solution was extracted twice more with 1:1 tetrahydrofuran/diethylether
  4. washthe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-55bedb1e267d49e1bb9fad90c2de5e97
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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