Hydrochloric Acid → 4-(5-Amino-3-methylpyridin-2-yl)cyclohex-3-en-1-ol

HRID 1748533ノート

反応式

HRID 1748533 の反応式
Br[C:2]1[CH:3]=[C:4]([CH3:22])[C:5]([C:8]2[CH2:13][CH2:12][CH:11]([O:14][Si](C(C)(C)C)(C)C)[CH2:10][CH:9]=2)=[N:6][CH:7]=1.C(=[NH:36])(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+].Cl>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C.O>[NH2:36][C:2]1[CH:3]=[C:4]([CH3:22])[C:5]([C:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH:9]=2)=[N:6][CH:7]=1

参加物

10

反応物 4

HCID 313Hydrochloric AcidHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 866924835-Bromo-2-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohex-1-en-1-yl)-3-methylpyridine

生成物 1

HCID 866924844-(5-Amino-3-methylpyridin-2-yl)cyclohex-3-en-1-ol収率 84.4%

試薬・触媒・溶媒 5

HCID 167845palladium(II) acetate触媒HCID 634876Binap, (A+-)-触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

A suspension of 5-bromo-2-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohex-1-en-1-yl)-3-methylpyridine (5.59 g) of Reference Example 110(1), benzophenonimine (2.77 g), palladium acetate (41 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (114 mg) and sodium tert-butoxide (2.1 g) in toluene (30 ml) was stirred under reflux for two hours. After completion of the reaction, the reaction solution was left stand, concentrated hydrochloric acid (20 ml) and water (60 ml) were added and stirred at room temperature for two hours. Then, diethyl ether was added and extracted with 1N hydrochloric acid aqueous solution. The resulting aqueous layer was cooled with ice, adjusted to pH>10 by the addition of 4N aqueous solution of sodium hydroxide and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated to give the titled compound (2.52 g) as a yellow solid.

後処理

  1. temperatureunder reflux for two hours
  2. customAfter completion of the reaction
  3. additionwere added
  4. stirringstirred at room temperature for two hours
  5. extractionextracted with 1N hydrochloric acid aqueous solution
  6. temperatureThe resulting aqueous layer was cooled with ice
  7. additionadjusted to pH>10 by the addition of 4N aqueous solution of sodium hydroxide
  8. extractionextracted with chloroform
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-f6c6e4fc55474f1cb5540333b67acafc
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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