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

HRID 1352199

Reaction equation

HRID 1352199 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c1a5dd50cd2541859680b41914f1deac
Source dataset
uspto-grants-2007_05
Patent number
US07220734B2

Linked notes

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