Triethylamine → HCID 66687867, compound

HRID 1895033Notes

Reaction equation

HRID 1895033 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11](O)[CH2:10][C@@:9]1([C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH2:14][CH2:15][CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:27]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.F.F.F.C(N(CC)CC)C.C(N(CC)CC)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([F:27])[CH2:10][C@:9]1([C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH2:14][CH2:15][CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 66687330(R)-2-(3,4-dichloro-benzoyl)-4-hydroxy-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66687867HCID 66687867, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (R)-2-(3,4-dichloro-benzoyl)-4-hydroxy-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.222 g, 0.554 mmol) in THF (3 mL) at ambient temperature under nitrogen was added perfluorobutanesulfonyl fluoride (0.195 mL, 1.11 mmol), triethylamine trihydrofluoride (0.181 mL, 1.11 mmol) and triethylamine (0.46 mL, 3.32 mmol). The reaction mixture was stirred for 18 hours, then filtered through a pad of silica, washed with EtOAc, and concentrated in vacuo to give (S)-2-(3,4-dichloro-benzoyl)-4-fluoro-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.222 g, 0.551 mmol, 99%) as a yellow foam that was used directly in the next step without further purification.

Workup

  1. filtrationfiltered through a pad of silica
  2. washwashed with EtOAc
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb03d3d4f2ef444283ed300741969483
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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