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

HRID 1352199

반응식

HRID 1352199 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c1a5dd50cd2541859680b41914f1deac
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220734B2

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