海萝胶 → benzyl N-[4-(2-aminoethyl)piperidine-1-carboximidoyl]carbamate

HRID 1450705

反应方程式

HRID 1450705 反应方程式
[BH4-].[Na+].[N:3]([CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[NH:26])[NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:10][CH2:9]1)=[N+]=[N-].Cl>O.O1CCCC1.[Pd]>[NH2:3][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[NH:26])[NH:15][C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:10][CH2:9]1

参与物

7

反应物 3

HCID 313海萝胶HCID 4311764硼氢化钠HCID 140379074benzyl N-[4-(2-azidoethyl)piperidine-1-carboximidoyl]carbamate

产物 1

HCID 140379088benzyl N-[4-(2-aminoethyl)piperidine-1-carboximidoyl]carbamate

试剂、催化剂与溶剂 3

HCID 23938钯催化剂2 次HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂3 次HCID 8028四氢呋喃溶剂

实验过程

To 30 ml of water was added 0.40 g of 10% Pd/C. Sodium borohydride, 1.0 g (0.031 mol), was dissolved in 30 ml of water and was added carefully to the stirred and ice-cooled slurry of Pd/C and water. 4-Azidoethyl-1-benzyloxycarbonylamidino piperidine, 2.9 g (8.8 mmol), was dissolved in 80 ml of tetrahydrofurane and this solution was added dropwise to the ice-cooled aqueous slurry above. After 4 h of stirring at room temperature the mixture was ice-cooled again and 30 ml of 2M HCl was added. The mixture was filtered through celite and the celite was rinsed with additional water. The tetrahydrofuran was evaporated and the aqueous phase was washed with ethyl acetate. The aqueous phase was made alkaline with 2M NaOH and extracted with methylene chloride three times. The combined organic phase was washed with water, dried (Na2SO4) and evaporated. The product was used in the following step without further purification.

后处理

  1. additionwas added carefully to the
  2. temperaturecooled aqueous slurry above
  3. stirringAfter 4 h of stirring at room temperature the mixture
  4. temperaturecooled again
  5. filtrationThe mixture was filtered through celite
  6. washthe celite was rinsed with additional water
  7. customThe tetrahydrofuran was evaporated
  8. washthe aqueous phase was washed with ethyl acetate
  9. extractionextracted with methylene chloride three times
  10. washThe combined organic phase was washed with water
  11. dry with materialdried (Na2SO4)
  12. customevaporated
  13. customThe product was used in the following step without further purification

来源与证据

ORD记录
ord-39ad06abf1904082bc3f4647d3099b3e
来源数据集
uspto-grants-1997_02
专利号
US05602253

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