吲哚-6-甲醛 → 吲哚

HRID 14325

反应方程式

HRID 14325 反应方程式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](C=O)[CH:8]=2)[CH:3]=[CH:2]1.C(O)(=O)C.NC[C@@H](O)[C@@H](NC(=O)OC(C)(C)C)CC1C=C(F)C=C(F)C=1.[BH4-].[Na+]>CC(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

参与物

5

反应物 3

HCID 2773435吲哚-6-甲醛HCID 4311764硼氢化钠HCID 86594203HCID 86594203，化合物

产物 1

HCID 798吲哚收率 62.8%

试剂、催化剂与溶剂 1

HCID 3776异丙醇溶剂

实验过程

To a stirred solution of 1H-indole-6-carbaldehyde (99 mg, 0.68 mmol) and tert-butyl (1S,2R)-3-amino-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate acetate 3 (256 mg, 0.68 mmol) in 2-propanol (3 mL) was added sodium borohydride (30 mg, 0.82 mmol). The reaction mixture was stirred for 12 h., quenched with methanol, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes) provided indole (50 mg): 1H NMR (300 MHz, CDCl3) δ 8.41 (br s, 1H), 7.60 (d, J=8 Hz, 1H), 7.38 (s, 1H), 7.21 (t, J=3 Hz, 1H), 7.04 (dd, J=8, 1 Hz, 1H), 6.71-6.73 (m, 3H), 6.61-6.68 (m, 1H), 6.53 (s, 1H), 5.38 (br s, 2H), 4.66 (d, J=9 Hz, 1H), 3.89 (s, 2H), 3.49-3.54 (m, 1H), 2.91-2.98 (m, 1H), 2.62-2.73 (m, 3H), 1.35 (s, 9H).

后处理

  1. customquenched with methanol
  2. concentrationconcentrated under reduced pressure
  3. customPurification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)

来源与证据

ORD记录
ord-b5d89e8898184893be2e9ad5c582c649
来源数据集
uspto-grants-2010_06
专利号
US07727997B2

关联笔记

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