四氢呋喃-3-羧醛 → HCID 178424141，化合物

HRID 59775

反应方程式

HRID 59775 反应方程式
[C:1]1([CH3:25])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][C@H:18]3[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]3)[CH:13]=2)[O:8]1.[O:26]1[CH2:30][CH2:29][CH:28]([CH:31]=O)[CH2:27]1.[C:33]([BH3-])#[N:34].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+]>[O:26]1[CH2:30][CH2:29][CH:28]([CH2:31][NH:24][C@H:21]2[CH2:20][CH2:19][C@H:18]([O:17][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[O:8][CH:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:25])[CH2:16][CH2:15]4)[CH2:23][CH2:22]2)[CH2:27]1.[O:26]1[CH2:30][CH2:29][CH:28]([CH2:31][N:34]([CH2:33][CH:28]2[CH2:29][CH2:30][O:26][CH2:27]2)[C@H:21]2[CH2:22][CH2:23][C@H:18]([O:17][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[O:8][CH:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:25])[CH2:16][CH2:15]4)[CH2:19][CH2:20]2)[CH2:27]1

参与物

8

反应物 3

HCID 157568四氢呋喃-3-羧醛HCID 5003444氰基硼氢化钠HCID 178424139HCID 178424139，化合物

产物 2

HCID 178424141HCID 178424141，化合物HCID 178424142HCID 178424142，化合物

试剂、催化剂与溶剂 3

HCID 176醋酸溶剂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2 次HCID 516892碳酸氢钠溶剂

实验过程

To a solution of 61 mg trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexylamine (0.18 mmol) in 3 ml methanol and 0.2 ml of acetic acid at room temperature 39 mg tetrahydrofuran-3-carboxaldehyde (0.20 mmol) in 3 ml of methanol were added, and 12 mg of sodium cyanoborohydride (0.89 mmol (0.20 mmol) were then added in one portion. Stirring at room temperature was continued for 16 h. The solution was diluted with aqueous saturated sodium hydrogencarbonate solution and the aqueous layer extracted with dichloromethane. The combined organic layers were dried with sodium sulfate and filtered, and the solvent removed under reduced pressure. The crude product was purified by RP-HPLC. 23 mg of (tetrahydrofuran-3-ylmethyl)-[trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexyl]-amine and 19 mg of bis-(tetrahydrofuran-3-ylmethyl)-[trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexyl]-amine were isolated.

后处理

  1. extractionthe aqueous layer extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe crude product was purified by RP-HPLC

来源与证据

ORD记录
ord-49890fe6d6d0441ab752901cbf80fecd
来源数据集
uspto-grants-2016_09
专利号
US09440941B2

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