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

HRID 365277노트

반응식

HRID 365277 반응식
[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]

참가 물질

6

반응물 1

HCID 69900746Boc4-aminomethylbicyclo-[2.2.2]octane nitrile

생성물 1

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

시약·촉매·용매 4

HCID 345198Adams' catalyst촉매HCID 176Acetic Acid용매HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b85fda91fe144eaaa5d806cb08dd4026
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127333

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