N~1~-(Pyridin-2-yl)ethane-1,2-diamine → Ethyl 2-[4-[2-(2-pyridylamino)ethylamino]cyclohexyl]acetate

HRID 1486175노트

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HRID 1486175 반응식
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.O=[C:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:13]1.[BH4-].[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.ClCCl>[N:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[NH:4][CH2:3][CH2:2][NH:1][CH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:13]1

참가 물질

6

반응물 3

HCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 4311764Sodium borohydrideHCID 12666966Ethyl 2-(4-oxocyclohexyl)acetate

생성물 1

HCID 86722966Ethyl 2-[4-[2-(2-pyridylamino)ethylamino]cyclohexyl]acetate

시약·촉매·용매 2

HCID 76524Titanium tetraethoxide촉매HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

To a mixture of 2-(N-[2-(amino)-ethyl]-amino)-pyridine (685 mg, 5 mmol) and ethyl 2-(4-oxocyclohexyl)acetate (786 mg, 4 mmol) was added dichloromethane (4 mL) followed by titanium ethoxide (420 μL, 2 mmol, technical grade). The resulting mixture was stirred for 4 hr then concentrated under reduced pressure. The residue was taken up in methanol (10 mL) and cooled to −78° C. To this solution was added sodium borohydride (228 mg, 6 mmol). On complete addition, the cold bath was removed and stirring continued for 1.25 hr. The mixture was diluted with dichloromethane and poured into saturated sodium carbonate solution (15 mL). The organic phase was separated, dried over magnesium sulfate and concentrated to give the crude title compound as a 6:1 mixture trans:cis isomers. This mixture was used without further purification.

후처리

  1. concentrationthen concentrated under reduced pressure
  2. additionOn complete addition
  3. customthe cold bath was removed
  4. stirringstirring
  5. waitcontinued for 1.25 hr
  6. additionThe mixture was diluted with dichloromethane
  7. additionpoured into saturated sodium carbonate solution (15 mL)
  8. customThe organic phase was separated
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-73f9a7b24e934499ad5296dcffb41a8b
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422314B2

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