Hydrochloric Acid → Adamantan-2-yl-isopropyl-amine

HRID 1393045ノート

反応式

HRID 1393045 の反応式
Cl.[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[C:3]1=O)[CH2:9]2.[CH:13]([NH2:16])([CH3:15])[CH3:14].C([BH3-])#N.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH:16][CH:13]([CH3:15])[CH3:14])[CH2:9]2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 64151AdamantanoneHCID 2724287Tetrabutylammonium (cyano-C)trihydroborate

生成物 1

HCID 43406547Adamantan-2-yl-isopropyl-amine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methanolic HCl (2.5 M; 13.3 mmol) is added to a solution of 2-adamantanone (1.00 g, 6.7 mmol) in dichloromethane (25 mL) and then isopropylamine (2.5 mL, 29.4 mmol) is added, followed by tetrabutylammonium cyanoborohydride (1.41 g, 5 mmol) and approximately 1 g of 4A molecular sieves. The reaction mixture is stirred at room temperature until the reaction is complete, as judged by TLC. Then the mixture is filtered and the filtrate is acidified to pH 1 with 1 M HCl, and the solvent is evaporated. The residue is taken up in water and extracted with ether. The aqueous layer is made basic to pH 10 with NaOH solution and the resulting mixture is extracted several times with ether. The combined ether layers are washed with water and brine, dried (magnesium sulfate), filtered, and evaporated to give adamantan-2-yl-isopropyl-amine.

後処理

  1. filtrationThen the mixture is filtered
  2. customthe solvent is evaporated
  3. extractionextracted with ether
  4. extractionthe resulting mixture is extracted several times with ether
  5. washThe combined ether layers are washed with water and brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-db52c959e4af456d85dcdaea4184d317
出典データセット
uspto-grants-2008_03
特許番号
US07345058B2

反応ノート

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