Sodium Cyanide → 1-Benzylpyrrolidine-3-carbonitrile

HRID 491510

반응식

HRID 491510 반응식
S([O-])(=O)(=O)C.[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15](O)[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C-:19]#[N:20].[Na+]>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15]([C:19]#[N:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

6

반응물 3

HCID 8929Sodium CyanideHCID 69889N-benzyl-3-pyrrolidinolHCID 85257Methanesulfonate

생성물 1

HCID 46745791-Benzylpyrrolidine-3-carbonitrile수율 75.7%

시약·촉매·용매 2

HCID 165872Tetrabutylammonium Cyanide촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
82.5 °C

실험 절차

This transformation was carried out using the method described in C. Thomas et. al. reference 97. The mesylate of racemic 1-benzyl-pyrrolidin-3-ol (0.039 mol, 10 g), prepared as described above, sodium cyanide (0.24 mol, 15 g) and tetrabutylammonium cyanide (10 g, 0.037 mol) in 75 mL of DMSO was stirred at 80-85° C. for 16 h. The reaction mixture was partitioned between diethyl ether and sat. aq sodium bicarbonate. The aqueous layer was extracted twice with ether and the combined organic layer was washed successively with sodium bicarbonate, water, and sat aq. NaCl. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and purified by flash chromatography over silica gel using a gradient of 20 to 30% ethyl acetate in hexane to afford 5.5 g of the desired product.

후처리

  1. customThe reaction mixture was partitioned between diethyl ether and sat. aq sodium bicarbonate
  2. extractionThe aqueous layer was extracted twice with ether
  3. washthe combined organic layer was washed successively with sodium bicarbonate, water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. custompurified by flash chromatography over silica gel using a gradient of 20 to 30% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-178c84c80efa45d59f6e2a8c7ccc7419
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531552B2

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