Pyridine → Benzyl-(2S)-2-aminocarbonyl4,4-difluoropyrrolidine-1-carboxylate

HRID 1161936Notes

Reaction equation

HRID 1161936 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C:17]([F:20])([F:19])[CH2:16][C@H:12]1[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:21]1C=CC=CC=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)(O)[O-].[NH4+]>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C:17]([F:20])([F:19])[CH2:16][C@H:12]1[C:13]([NH2:21])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 53909714(S)-1-((Benzyloxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

Product 1

HCID 58786847Benzyl-(2S)-2-aminocarbonyl4,4-difluoropyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1-[(benzyloxy)carbonyl]-4,4-difluoro-L-proline, pyridine (0.6 eq.) and di-t-butyl dicarbonate (1.3 eq) in dioxane, ammonium bicarbonate (1.26 eq) was added and the mixture was stirred at room temperature for 20 hours. Dioxane was concentrated and the residue dissolved in ethyl acetate and washed with HCl 1 N, saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and evaporated in vacuo to obtain a yellow oil.

Workup

  1. concentrationDioxane was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with HCl 1 N, saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto obtain a yellow oil

Sources & evidence

ORD record
ord-80fba971d930416ab7a37d079e3b4cfc
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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