Trifluoroacetic acid → HCID 69480725, compound

HRID 856039Notes

Reaction equation

HRID 856039 reaction equation
[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2C(OC(C)(C)C)=O)=[CH:6][CH:5]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:24][C:2]([F:1])([F:25])[O:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][NH:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69635179HCID 69635179, compound

Product 1

HCID 69480725HCID 69480725, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl (S)-2-(4-trifluoromethoxyphenoxymethyl)pyrrolidine-1-carboxylate (2.31 g, 6.39 mmol) prepared in Reference Example 62, trifluoroacetic acid (20 ml), and methylene chloride (20 ml) was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was neutralized with 10% sodium hydroxide aqueous solution and the mixture was extracted with methylene chloride, and the extract was dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to afford (S)-2-(4-trifluoromethoxyphenoxymethyl)-pyrrolidine (1.65 g, yield 99%) as a pale brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe mixture was extracted with methylene chloride
  3. dry with materialthe extract was dried over magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4bbb3b418e8544fcb6f12976a5ed1ef9
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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