Triethylborane → (S)-tert-Butyl 2-(3-(perfluorophenoxysulfonyl)propyl)pyrrolidine-1-carboxylate

HRID 1643453ノート

反応式

HRID 1643453 の反応式
[PH2](O)=O.C(N1CCCCC1)C.[CH2:12]=[CH:13][S:14]([O:17][C:18]1[C:23]([F:24])=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28])(=[O:16])=[O:15].I[CH2:30][C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].C(B(CC)CC)C>C(Cl)Cl>[F:24][C:23]1[C:22]([F:25])=[C:21]([F:26])[C:20]([F:27])=[C:19]([F:28])[C:18]=1[O:17][S:14]([CH2:13][CH2:12][CH2:30][C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])(=[O:16])=[O:15]

参加物

6

反応物 4

HCID 7357Triethylborane2 回HCID 2763990Pentafluorophenyl vinylsulfonateHCID 11312942(S)-2-Iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178462538HCID 178462538、化合物

生成物 1

HCID 59367744(S)-tert-Butyl 2-(3-(perfluorophenoxysulfonyl)propyl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-Ethylpiperidine hypophosphite (30 g, 168 mmol) were weighed into the reaction flask under an inert gas, and methylene chloride (100 ml) was added. The solution was cooled with ice-water and 2,3,4,5,6-pentafluorophenyl 1-ethylenesulfonate (5.06 g, 18.5 mmol) [Org. Lett.; 2002; 4(15); 2549-2551] and (S)-tert-butyl 2-(iodomethyl)pyrrolidine-1-carboxylate (5.22 g, 16.8 mmol) was added at 10° C. Triethylborane solution (1.6 ml, 1 mol/l) was added and compressed air was then passed through the mixture for 5 sec. After stirring for min the addition of triethylborane solution-compressed air was repeated with the same amount. The cooling bath was removed, the mixture was stirred for 10 min and the reaction mixture was then washed with water (20 ml) and saturated sodium chloride solution (20 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/diethyl ether (2:1). Yield: 2.81 g (36%)

後処理

  1. additionwas added
  2. additionwas added at 10° C
  3. customThe cooling bath was removed
  4. stirringthe mixture was stirred for 10 min
  5. washthe reaction mixture was then washed with water (20 ml) and saturated sodium chloride solution (20 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (silica gel) with hexane/diethyl ether (2:1)

出典と根拠

ORDレコード
ord-cc80e06a145948fcb30a60cc2204b22e
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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