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Sodium Bicarbonate → 8-(5-Aminopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester

HRID 1748505
ノート
印刷プレビュー

反応式

HRID 1748505 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH2:29]([O:31][C:32]([C:34]1([C:44]2[CH:49]=[CH:48][C:47](Br)=[CH:46][N:45]=2)[CH2:43][CH2:42][C:37]2([O:41][CH2:40][CH2:39][O:38]2)[CH2:36][CH2:35]1)=[O:33])[CH3:30].[F-].C([N+:56](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:29]([O:31][C:32]([C:34]1([C:44]2[CH:49]=[CH:48][C:47]([NH2:56])=[CH:46][N:45]=2)[CH2:43][CH2:42][C:37]2([O:41][CH2:40][CH2:39][O:38]2)[CH2:36][CH2:35]1)=[O:33])[CH3:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 2733832Lithium hexamethyldisilazaneHCID 44558591Tri-t-butylphosphine fluoroborateHCID 86692455HCID 86692455、化合物

生成物 1

HCID 866924568-(5-Aminopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒2 回

実験手順

1.0M Toluene-solution of lithium bis(trimethylsilyl)amide (1.89 ml) was added to bis(dibenzylideneacetone)palladium (0) (39 mg) and tri-tert-butylphosphine tetrafluoroborate (20 mg) at 70° C. under an atmosphere of nitrogen, a solution of 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester (500 mg) in toluene (1.4 ml) was added dropwise and stirred at the same temperature for 0.5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, tetrabutylammonium fluoride (4.7 ml) was added and stirred at the same temperature for an hour. Then, a saturated aqueous solution of sodium bicarbonate was added and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (312 mg) as a yellow oil.

後処理

  1. customAfter completion of the reaction
  2. stirringstirred at the same temperature for an hour
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-0ebde3beb7ac4ac496e01e8582b1827b
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150555B2

反応ノート

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