3-氨基-1-丙醇 → 3-[(Anthracen-9-ylmethyl)-amino]-propan-1-OL

HRID 13002

反应方程式

HRID 13002 反应方程式
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[CH:6]1[C:19]2[C:10](=[CH:11][C:12]3[C:17]([C:18]=2[CH:20]=O)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:8][CH:7]=1.[BH4-].[Na+]>CO.C(Cl)Cl>[CH:16]1[C:17]2[C:12](=[CH:11][C:10]3[C:19]([C:18]=2[CH2:20][NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:13]=[CH:14][CH:15]=1

参与物

5

反应物 3

HCID 90863-氨基-1-丙醇HCID 695049-蒽甲醛HCID 4311764硼氢化钠

产物 1

HCID 114710953-[(Anthracen-9-ylmethyl)-amino]-propan-1-OL收率 78%

试剂、催化剂与溶剂 1

HCID 21226129Dichloromethane methanol溶剂2 次

反应条件

温度
0 °C

实验过程

To a stirred solution of 3-amino -1-propanol, 15a (0.87 g, 11.65 mmol) in 25% MeOH/CH2Cl2 (20 mL), was added a solution of aldehyde 8 (2.00 g, 9.7 mmol) in 25% MeOH/CH2Cl2 (15 mL) under N2. The mixture was stirred at room temperature overnight until the imine formation was complete (monitored by NMR). The solvent was removed in vacuo, the solid residue dissolved in 50% MeOH/CH2Cl2 (40 mL) and the solution was cooled to 0° C. NaBH4 (29.1 mmol) was added in small portions to the solution and the mixture was stirred at rt overnight. The solvent was removed in vacuo, the solid residue dissolved in CH2Cl2 (40 mL) and washed with 10% aq. Na2CO3 solution (3×30 mL). The CH2Cl2 layer was separated, dried over anhydrous Na2SO4, filtered and removed in vacuo to give an oily residue. The oil was purified by flash column chromatography (6% MeOH/CHCl3) to yield the product 14a as a pale yellow thick oil (78%), Rf=0.3 (6% MeOH/CHCl3); 1H NMR (CDCl3) δ 8.39 (s, 1H), 8.27 (d, 2H), 7.99 (d, 2H), 7.52 (m, 2H), 7.45 (m, 2H), 4.71 (s, 2H), 3.79 (t, 2H), 3.09 (t, 2H), 1.74 (q, 2H).

后处理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe solid residue dissolved in 50% MeOH/CH2Cl2 (40 mL)
  3. customThe solvent was removed in vacuo
  4. dissolutionthe solid residue dissolved in CH2Cl2 (40 mL)
  5. washwashed with 10% aq. Na2CO3 solution (3×30 mL)
  6. customThe CH2Cl2 layer was separated
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customremoved in vacuo
  10. customto give an oily residue
  11. customThe oil was purified by flash column chromatography (6% MeOH/CHCl3)

来源与证据

ORD记录
ord-30f1992baf034a71a92d713868cde3b2
来源数据集
uspto-grants-2010_06
专利号
US07728041B2

关联笔记

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