Sodium Fluoride → tert-butyl(2R)-2-[(dimethylamino)carbonyl]-4-fluoropyrrolidine-1-carboxylate

HRID 490133

反応式

HRID 490133 の反応式
[F:1]C(F)(N(CC)CC)C(F)C(F)(F)F.[CH3:15][N:16]([CH3:32])[C:17]([C@H:19]1[CH2:23][C@@H:22](O)[CH2:21][N:20]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:18].[F-].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(OCC)(=O)C>[CH3:15][N:16]([CH3:32])[C:17]([C@H:19]1[CH2:23][CH:22]([F:1])[CH2:21][N:20]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:18]

参加物

7

反応物 4

HCID 5235Sodium FluorideHCID 11430Potassium CarbonateHCID 136149N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamineHCID 58815374Tert-butyl (2R,4R)-2-(dimethylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

生成物 1

HCID 69064202tert-butyl(2R)-2-[(dimethylamino)carbonyl]-4-fluoropyrrolidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2.89 g of a mixture (approximately 3:1) of 1,1,2,3,3,3-hexafluoro-1-(diethylamino)propane and 1,2,3,3,3-pentafluoro-1-(diethylamino)-2-propene was added dropwise over a period of 10 minutes, and under ice cooling, to a suspension of 2.64 g of the compound obtained in step 6-1 and 545 mg of sodium fluoride in 26 mL of dichloromethane, after which the reaction mixture was stirred for 16 hours at room temperature. After this, 100 mL of a 5% potassium carbonate aqueous solution was added under ice cooling to the reaction solution, and the reaction mixture was stirred for 30 minutes at the same temperature. After liquid separation, the aqueous layer thus obtained was extracted with chloroform (30 mL×2), and the combined organic layer was washed with 50 mL of saturated brine and dried with magnesium sulfate, after which the drying agent was filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to column chromatography (silica gel 60, mobile phase: ethyl acetate) to obtain 2.17 g of the titled compound (colorless solid).

後処理

  1. stirringthe reaction mixture was stirred for 30 minutes at the same temperature
  2. customAfter liquid separation
  3. customthe aqueous layer thus obtained
  4. extractionwas extracted with chloroform (30 mL×2)
  5. washthe combined organic layer was washed with 50 mL of saturated brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationafter which the drying agent was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue thus obtained

出典と根拠

ORDレコード
ord-338b936ee2b44320b924c4e3d66dcc28
出典データセット
uspto-grants-2009_05
特許番号
US07528124B2

関連ノート

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