Ammonium formate → HCID 25143663, compound

HRID 1931804Notes

Reaction equation

HRID 1931804 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)([F:13])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO>[F:21][C:16]1[CH:15]=[C:14]([C:10]2([F:13])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:19]=[C:18]([F:20])[CH:17]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 68519937HCID 68519937, compound

Product 1

HCID 25143663HCID 25143663, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-benzyl-3-(3,5-difluorophenyl)-3-fluoropyrrolidine (0.65 g, 2.2 mmol) and ammonium formiate (1.4 g, 22 mmol) in methanol (50 mL) was purged with nitrogen and palladium on carbon (65 mg) was added. The mixture was refluxed for 8 h and palladium on carbon (30 mg) was added at 4 h, 6 h and 7 h respectively. The mixture was cooled to ambient temperature and filtered through a pad of celite. The filtrate was evaporated, aqueous sodium carbonate (10%, 50 mL) was added and the aqueous phase was extracted with dichloromethane (2×50 mL). Purification by flash column chromatography on silica gel (ethyl acetate/methanol, 1:1 to 0:1) gave the title compound (0.14 g). The amine was converted to the oxalic acid salt and recrystallized from methanol/diethyl ether: M.p. 176-177° C.; MS m/z (relative intensity, 70 eV) 201 (M+, bp), 181 (20), 180 (29), 158 (21), 151 (53).

Workup

  1. customwas purged with nitrogen and palladium on carbon (65 mg)
  2. additionwas added
  3. temperatureThe mixture was refluxed for 8 h
  4. additionpalladium on carbon (30 mg) was added at 4 h, 6 h and 7 h respectively
  5. filtrationfiltered through a pad of celite
  6. customThe filtrate was evaporated
  7. additionaqueous sodium carbonate (10%, 50 mL) was added
  8. extractionthe aqueous phase was extracted with dichloromethane (2×50 mL)
  9. customPurification by flash column chromatography on silica gel (ethyl acetate/methanol, 1:1 to 0:1)

Sources & evidence

ORD record
ord-c55a4f1825a347ba91e444944e51a48a
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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