1H-Indole-6-carboxaldehyde → Indole

HRID 14325

反応式

HRID 14325 の反応式
[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

参加物

5

反応物 3

HCID 27734351H-Indole-6-carboxaldehydeHCID 4311764Sodium borohydrideHCID 86594203HCID 86594203、化合物

生成物 1

HCID 798Indole収率 62.8%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-b5d89e8898184893be2e9ad5c582c649
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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