Boc4-aminomethylbicyclo-[2.2.2]octane nitrile → Boc-4-aminomethylbicyclo-[2.2.2]octane methylamine

HRID 365277

反応式

HRID 365277 の反応式
[C:1]([CH:8]1[CH2:13][C:12]2([CH2:16][NH2:17])[CH2:14][CH2:15][C:9]1([C:18]#[N:19])[CH2:10][CH2:11]2)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CO.CC(O)=O.O.O=[Pt]=O>[C:1]([CH:8]1[CH2:13][C:12]2([CH2:16][NH2:17])[CH2:11][CH2:10][C:9]1([CH2:18][NH2:19])[CH2:15][CH2:14]2)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

参加物

6

反応物 1

HCID 69900746Boc4-aminomethylbicyclo-[2.2.2]octane nitrile

生成物 1

HCID 131722017Boc-4-aminomethylbicyclo-[2.2.2]octane methylamine

試薬・触媒・溶媒 4

HCID 345198Adams' catalyst触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of 6.75 g (25.5 mmol) of the product from step D in 200 ml of CH3OH plus 4 ml of HOAc and 2 ml of H2O was hydrogenated over 1.63 g of PtO2 in a Parr shaker at 55 psi for 22 hr. The catalyst was removed by filtration through Celite, and the filtrate was concentrated in vacuo to an oily residue, which was flushed/evaporated with CH3OH (1×) and CH2Cl2 (2×). Product began to crystallize toward the end of the evaporation, and ether (up to 300 ml) was added to complete the precipitation. The white solid was triturated and isolated by filtration and washing with ether to give, after drying in vacuo, the title compound as the acetate salt.

後処理

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated in vacuo to an oily residue, which
  3. customwas flushed/evaporated with CH3OH (1×) and CH2Cl2 (2×)
  4. customto crystallize toward the end of the evaporation, and ether (up to 300 ml)
  5. additionwas added
  6. customthe precipitation
  7. customThe white solid was triturated
  8. customisolated by filtration
  9. washwashing with ether
  10. customto give
  11. customafter drying in vacuo

出典と根拠

ORDレコード
ord-b85fda91fe144eaaa5d806cb08dd4026
出典データセット
uspto-grants-2000_10
特許番号
US06127333

関連ノート

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