Tetrabutylammonium Fluoride → (S)-tert-Butyl 2-(fluoromethyl)pyrrolidine-1-carboxylate

HRID 494884

Reaction equation

HRID 494884 reaction equation
CS(O[CH2:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)=O.[F-:19].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:19][CH2:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10039261tert-butyl (2S)-2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylate

Product 1

HCID 86586409(S)-tert-Butyl 2-(fluoromethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 164A (7 g) in 100 mL of THF and tetrabutylammonium fluoride (42 mL of a 1M solution in THF) was heated at reflux for 17 hours, cooled, concentrated to dryness, diluted with 125 mL of ethyl acetate, washed with 5% aqueous NaHCO3, brine, dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure to provide an oil. The oil was distilled in vacuo (50° C., 1.2 torr) to give 4.9 g of the title compound as a colorless oil.

Workup

  1. temperatureat reflux for 17 hours
  2. temperaturecooled
  3. concentrationconcentrated to dryness
  4. additiondiluted with 125 mL of ethyl acetate
  5. washwashed with 5% aqueous NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customto provide an oil
  10. distillationThe oil was distilled in vacuo (50° C., 1.2 torr)

Sources & evidence

ORD record
ord-3632172ee19647fa92f7735f0b043926
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Linked notes

Loading…