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

HRID 494884

반응식

HRID 494884 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3632172ee19647fa92f7735f0b043926
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538138B2

연결된 노트

불러오는 중…