异丙醇胺 → HCID 17332070，化合物

HRID 839812

反应方程式

HRID 839812 反应方程式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:15][CH2:16][CH:17]([OH:19])[CH3:18].[BH4-].[Na+]>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:14][C:11]([CH2:12][NH:15][CH2:16][CH:17]([OH:19])[CH3:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

参与物

5

反应物 3

HCID 4异丙醇胺HCID 6761845-(4-氯苯基)糠醛HCID 4311764硼氢化钠

产物 1

HCID 17332070HCID 17332070，化合物收率 99.3%

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

实验过程

5-(4-Chlorophenyl)furfural (42 g, 0.20 mole) was added in portions to a solution of 15 g (0.20 mole) of 1-amino-2-propanol in 200 ml of methanol with stirring at room temperature. The mixture was stirred for 0.5 hr., heated under reflux for 1.5 hr., and allowed to stand overnight. To this solution 7.6 g (0.20 mole) of sodium borohydride was added in portions over 1 hr. at 15°-20°. The solution was stirred at ambient temperature for 1 hr. and heated under reflux for 0.5 hr. The solvent was removed on a rotary evaporator, and the residual solid was partitioned between chloroform and water. The layers were separated, and the aqueous layer was extracted once with chloroform. The combined chloroform layers were dried over MgSO4 and concentrated on a rotary evaporator. The residual solid was dissolved in 150 ml of absolute methanol with warming and was treated with 40 ml of methanolic HCl with cooling. Anhydrous ether (1 1.) was added, and the solid which was deposited was collected by filtration to give 30 g (50%) of 1-[5-(4-chlorophenyl)furfurylamino]-2-propanol hydrochloride. One recrystallization from CH3CN gave an analytical sample; m.p. 197°-202°.

后处理

  1. stirringThe mixture was stirred for 0.5 hr
  2. temperature, heated
  3. temperatureunder reflux for 1.5 hr
  4. customat 15°-20°
  5. stirringThe solution was stirred at ambient temperature for 1 hr
  6. temperatureand heated
  7. temperatureunder reflux for 0.5 hr
  8. customThe solvent was removed on a rotary evaporator
  9. customthe residual solid was partitioned between chloroform and water
  10. customThe layers were separated
  11. extractionthe aqueous layer was extracted once with chloroform
  12. dry with materialThe combined chloroform layers were dried over MgSO4
  13. concentrationconcentrated on a rotary evaporator
  14. dissolutionThe residual solid was dissolved in 150 ml of absolute methanol
  15. temperaturewith warming
  16. additionwas treated with 40 ml of methanolic HCl
  17. temperaturewith cooling
  18. additionAnhydrous ether (1 1.) was added
  19. filtrationthe solid which was deposited was collected by filtration

来源与证据

ORD记录
ord-a0065273a616495bbb5ac8993c3cbe6f
来源数据集
uspto-grants-1978_06
专利号
US04097499

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