Trifluoroacetic acid → Ammonia

HRID 1985716Notes

Reaction equation

HRID 1985716 reaction equation
C(OC([N:8]1[CH2:20][C@@H:19]2[N:11]([C:12]3[N:13]=[C:14]4[C@H:23]([CH3:24])[O:22][CH2:21][C:15]4=[CH:16][C:17]=3[CH2:18]2)[C@H:10]([CH3:25])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[NH3:8].[CH3:24][C@H:23]1[C:14]2[C:15](=[CH:16][C:17]3[CH2:18][C@H:19]4[N:11]([C:12]=3[N:13]=2)[C@H:10]([CH3:25])[CH2:9][NH:8][CH2:20]4)[CH2:21][O:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67237767HCID 67237767, compound

Product 2

HCID 222AmmoniaHCID 11997368HCID 11997368, compound

Procedure

The product of step 1 was treated with trifluoroacetic acid at 0° C. for 30 minutes. The mixture was evaporated under aspirator vacuum and the residue was partitioned between water and ethyl acetate. The phases were separated and the aqueous phase was mixed with dichloromethane. The pH of this mixture was adjusted to 12.00 by addition of 28% aqueous sodium hydroxide. The phases were separated and the organic phase was washed with half concentrated brine dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel with methylenechloride:methanol:ammonia=90:10:1 to yield the title compound (3S,5R,8aR)-3,5-Dimethyl-1,3,5,6,7,8,8a,9-octahydro-2-oxa-4,4b,7-triaza-cyclopenta[b]fluorene as slightly yellow crystals m.p.: 90-91° C.

Workup

  1. customThe mixture was evaporated under aspirator vacuum
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe phases were separated
  4. additionthe aqueous phase was mixed with dichloromethane
  5. additionThe pH of this mixture was adjusted to 12.00 by addition of 28% aqueous sodium hydroxide
  6. customThe phases were separated
  7. washthe organic phase was washed with half concentrated brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customThe residue was purified by chromatography on silica gel with methylenechloride

Sources & evidence

ORD record
ord-1b63f42150174208aa21b063348a1363
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

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