Trifluoroacetic acid → (2S)-2-(phenoxymethyl)pyrrolidine

HRID 2186473Notes

Reaction equation

HRID 2186473 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[O:14]([CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 10636271(S)-tert-Butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 9855629(2S)-2-(phenoxymethyl)pyrrolidineYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-(+)-N-Boc-2-phenoxymethylpyrrolidine (0.81 g. 2.9 mmol) in 5 mL of CH2Cl2 in 0° C. was added 5 mL of TFA dropwise over 1 hour. The solution was warmed to room temperature and stirred for 1.5 hours. The reaction mixture was slowly poured into 30 mL of 10% NaOH and extracted thrice with 20 mL CH2Cl2. The organic layer was then dried over Na2SO4, filtered and concentrated under reduced pressure to give a light yellow oil (0.41 g, 79%). ES (+) MS m/e=178 (M+H).

Workup

  1. extractionextracted thrice with 20 mL CH2Cl2
  2. dry with materialThe organic layer was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39b6952065504f61b163ddc4571c2dcb
Source dataset
uspto-grants-2002_06
Patent number
US06403792B1

Reaction notes

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