3-Amino-1-propanol → 3-[(Anthracen-9-ylmethyl)-amino]-propan-1-OL

HRID 13002

反応式

HRID 13002 の反応式
[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

参加物

5

反応物 3

HCID 90863-Amino-1-propanolHCID 695049-AnthracenecarboxaldehydeHCID 4311764Sodium borohydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-30f1992baf034a71a92d713868cde3b2
出典データセット
uspto-grants-2010_06
特許番号
US07728041B2

関連ノート

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