Triethylamine → HCID 67274435, compound

HRID 1163326Notes

Reaction equation

HRID 1163326 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[CH2:12]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@@H:20]([NH2:23])[CH2:19]1)=[O:17])[CH:13]=[CH2:14].C(N(CC)CC)C>C(OCC)(=O)C>[CH2:12]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@@H:20]([NH:23][C:7]2[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=2[F:1])[CH2:19]1)=[O:17])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 15839928HCID 15839928, compound

Product 1

HCID 67274435HCID 67274435, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 5.01 g of 3,4-difluoro nitrobenzene, 5.1 g (3R)-1-allyloxycarbonyl-3-amino pyrrolidine (30 mmol) and 6.27 ml of triethylamine (31.5 mmol) in 100 ml of ethyl acetate was stirred at reflux. The reaction was monitored by HPLC. The reaction was diluted with ethyl acetate, washed with water and brine, the org. layer dried over Mg sulfate, filtered and evaporated. The residue crystallized from an ether/hexane mixture.

Workup

  1. temperatureat reflux
  2. washwashed with water and brine
  3. dry with materiallayer dried over Mg sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue crystallized from an ether/hexane mixture

Sources & evidence

ORD record
ord-10034ece676e4f7883cb98dee1d6e5c4
Source dataset
uspto-grants-2010_10
Patent number
US07820823B2

Reaction notes

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