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

HRID 494884

反応式

HRID 494884 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3632172ee19647fa92f7735f0b043926
出典データセット
uspto-grants-2009_05
特許番号
US07538138B2

関連ノート

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