Triethylamine → Benzyl-(2S)-2-cyano-4,4-difluoropyrrolidine-1-carboxylate

HRID 1161937Notes

Reaction equation

HRID 1161937 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]([NH2:20])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[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:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 58786847Benzyl-(2S)-2-aminocarbonyl4,4-difluoropyrrolidine-1-carboxylate

Product 1

HCID 23626153Benzyl-(2S)-2-cyano-4,4-difluoropyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl-(2S)-2-aminocarbonyl-4,4-difluoropyrrolidine-1-carboxylate and triethylamine (2.1 eq.) in dichloromethane was cooled to 0° C. and trifluoroacetic anhydride (1.1 eq.) was added dropwise under nitrogen. Stirring was continued for 1 hour allowing the mixture to reach room temperature. Volatiles removed in vacuo and residue taken up in ethyl acetate, washed with HCl 1N, brine and dried over Na2SO4. Evaporation gave title compound as brown oil.

Workup

  1. customto reach room temperature
  2. customVolatiles removed in vacuo and residue
  3. washwashed with HCl 1N, brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation

Sources & evidence

ORD record
ord-a622ee6abba346deb8b79ab990578f1c
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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