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

HRID 1486175ノート

反応式

HRID 1486175 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 76524Titanium tetraethoxide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-73f9a7b24e934499ad5296dcffb41a8b
出典データセット
uspto-grants-2016_08
特許番号
US09422314B2

反応ノート

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