(Diethylamino)sulfur trifluoride → 1-Benzyl-3-(2,3-difluorophenyl)-3-fluoropyrrolidine

HRID 1931890ノート

反応式

HRID 1931890 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[F:21])(O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)[F:28])CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[F:21])([F:28])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 123472(Diethylamino)sulfur trifluoride2 回HCID 516892Sodium BicarbonateHCID 685158491-Benzyl-3-(2,3-difluorophenyl)pyrrolidin-3-ol

生成物 1

HCID 685171501-Benzyl-3-(2,3-difluorophenyl)-3-fluoropyrrolidine収率 37.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 1-benzyl-3-(2,3-difluorophenyl)pyrrolidin-3-ol (5.3 g, 18.3 mmol) in dichloromethane (30 mL) at 0° C. was added drop wise, a solution of diethylaminosulfur trifluoride (2.93 mL, 22.4 mmol) in dichloromethane. The cooling was removed and the mixture was stirred at ambient temperature for 2 h after which an additional amount of diethylaminosulfur trifluoride (0.1 mL, 0.76 mmol) was added. The mixture was stirred for 1 h at ambient temperature after which aqueous sodium hydrogen carbonate (10%) was added and the mixture was extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (isooctane/ethyl acetate, 1:0 to 1:1) gave the title compound (2 g). MS m/z (relative intensity, 70 eV) 291 (M+, 32), 200 (18), 133 (54), 91 (bp), 65 (20).

後処理

  1. customThe cooling was removed
  2. additionwas added
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash chromatography on silica gel (isooctane/ethyl acetate, 1:0 to 1:1)

出典と根拠

ORDレコード
ord-bcafeefc4a31439592de14fcf810e22c
出典データセット
uspto-grants-2012_05
特許番号
US08188301B2

反応ノート

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