1-oxo-2,3-dihydro-1H-indene-5-carbonitrile → 1-hydroxy-2,3-dihydro-1H-indene-5-carbonitrile

HRID 1352199

反応式

HRID 1352199 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2)#[N:2].[BH4-].[Na+]>CO.C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([OH:12])[CH2:7][CH2:6]2)#[N:2]

参加物

5

反応物 2

HCID 3128961-oxo-2,3-dihydro-1H-indene-5-carbonitrileHCID 4311764Sodium borohydride

生成物 1

HCID 145153231-hydroxy-2,3-dihydro-1H-indene-5-carbonitrile収率 71.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 5-cyano-1-indanone (3.40 g, 21.63 mmol, prepared according to Reich, S. H., et. al. J. Med. Chem., 2000, 43, 1670–1683) in methanol (50 mL) was treated with sodium borohydride (0.25 g, 6.48 mmol). After stirring for 3 h, the reaction was diluted with methylene chloride (50 mL) and washed with saturated aqueous sodium bicarbonate (50 mL). The aqueous layer was further extracted with methylene chloride (2 50 mL). The extracts were combined, dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography eluting with 40% ethyl acetate/hexanes gave 2.45 g (15.40 mmol, 71%) of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.48–7.54 (m, 3H), 5.25–5.29 (m, 1H), 3.03–3.10 (m, 2H), 2.81–2.89 (m, 2H), 2.52–2.59 (m, 2H), 1.94–2.01 (m, 2H); 13C NMR (CDCl3, 125 MHz) δ 150.1, 144.2, 130.9, 128.6, 125.0, 119.1, 111.8, 75.9, 35.8, 29.5.

後処理

  1. washwashed with saturated aqueous sodium bicarbonate (50 mL)
  2. extractionThe aqueous layer was further extracted with methylene chloride (2 50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. washSilica gel chromatography eluting with 40% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-c1a5dd50cd2541859680b41914f1deac
出典データセット
uspto-grants-2007_05
特許番号
US07220734B2

関連ノート

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