Triethylamine → Benzyl-(2S)-2-[amino(hydroxyimino)methyl]4,4-difluoropyrrolidine-1-carboxylate

HRID 1161938Notes

Reaction equation

HRID 1161938 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][C@H:12]1[C:18]#[N:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].C(N(CC)CC)C>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][C@H:12]1[C:18]([NH2:19])=[N:21][OH:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 23626153Benzyl-(2S)-2-cyano-4,4-difluoropyrrolidine-1-carboxylate

Product 1

HCID 86609167Benzyl-(2S)-2-[amino(hydroxyimino)methyl]4,4-difluoropyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of benzyl-(2S)-2-cyano-4,4-difluoropyrrolidine-1-carboxylate, hydroxylamine hydrochloride (1.4 eq.) and triethylamine (1.7 eq.) in ethanol was refluxed under nitrogen for 5 hours. Mixture was concentrated and residues taken up in ethyl acetate and washed with water and brine. Combined organics were dried over Na2SO4 and evaporated to give title compound as a foam.

Workup

  1. concentrationMixture was concentrated
  2. washwashed with water and brine
  3. dry with materialCombined organics were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-146cd6ac5367439dbf0f6501a8ab1ef7
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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