1,8-Diazabicyclo(5.4.0)undec-7-ene → (S)-tert-Butyl 2-(3-(4-(1-methylpiperidin-4-yl)piperazin-1-ylsulfonyl)propyl)pyrrolidine-1-carboxylate

HRID 1643454ノート

反応式

HRID 1643454 の反応式
FC1C(F)=C(F)C(F)=C(F)C=1O[S:5]([CH2:8][CH2:9][CH2:10][C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:7])=[O:6].[CH3:31][N:32]1[CH2:37][CH2:36][CH:35]([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:34][CH2:33]1.N12CCCN=C1CCCCC2.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:31][N:32]1[CH2:33][CH2:34][CH:35]([N:38]2[CH2:43][CH2:42][N:41]([S:5]([CH2:8][CH2:9][CH2:10][C@@H:11]3[CH2:15][CH2:14][CH2:13][N:12]3[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])(=[O:6])=[O:7])[CH2:40][CH2:39]2)[CH2:36][CH2:37]1

参加物

7

反応物 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 59367744(S)-tert-Butyl 2-(3-(perfluorophenoxysulfonyl)propyl)pyrrolidine-1-carboxylate

生成物 1

HCID 59367787(S)-tert-Butyl 2-(3-(4-(1-methylpiperidin-4-yl)piperazin-1-ylsulfonyl)propyl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(S)-tert-Butyl 2-(3-(perfluorophenoxysulfonyl)propyl)pyrrolidine-1-carboxylate (2.8 g, 6.099 mmol) and 1-(1-methylpiperidin-4-yl)piperazine (1.676 g, 9.148 mmol) were dissolved in tetrahydrofuran (40 ml), 1,8-diazabicyclo[5.4.0]undec-7-ene (2.7 ml, 18.297 mmol) was added under an inert gas and the mixture was refluxed for 2 h. Ethyl acetate and saturated sodium bicarbonate solution (50 ml of each) were added, the phases were separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with saturated sodium bicarbonate solution (40 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/methylene chloride/ammonia (25% aq) (300:100:50:1). Yield: quantitative

後処理

  1. temperaturethe mixture was refluxed for 2 h
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
  4. washThe combined organic phases were washed with saturated sodium bicarbonate solution (40 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/methylene chloride/ammonia (25% aq) (300:100:50:1)

出典と根拠

ORDレコード
ord-f335ffbf78ea4132a94ad5ff78a9dd92
出典データセット
uspto-grants-2012_02
特許番号
US08119805B2

反応ノート

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