Sodium hydride → HCID 67324479, compound

HRID 1257585Notes

Reaction equation

HRID 1257585 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:4]=1[CH2:5][NH:6][C:7](=[O:16])[CH2:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH:11]=[CH:10]1.[H-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH:14]2[CH:9]([CH2:10][CH2:11][C:12](=[O:15])[CH2:13]2)[CH2:8][C:7]1=[O:16]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67325684HCID 67325684, compound

Product 1

HCID 67324479HCID 67324479, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2,4-Dimethoxy-benzyl)-2-(4-oxo-cyclohex-2-enyl)-acetamide (469.8 mg, 1.549 mmol) in THF (15 mL) was added sodium hydride (60 wt % on mineral oil, 245 mg, 6.12 mmol). The reaction mixture was stirred at room temperature for one hour and then quenched with saturated aqueous ammonium chloride. The mixture was then extracted twice with dichloromethane, and the combined extracts dried over magnesium sulfate, filtered, and evaporated in vacuo. Purification by column chromatography on silica gel (gradient: 0 to 10% methanol in dichloromethane) yielded 365.0 mg (78%) of 1-(2,4-Dimethoxy-benzyl)-hexahydro-indole-2,6-dione. LCMS (Method E, ESI): RT=1.22 min, m+H=304.2; 1H NMR (400 MHz, CD3OD) δ: 7.11 (d, J=8.3 Hz, 1H), 6.53 (d, J=1.8 Hz, 1H), 6.48 (dd, J=8.3, 2.1 Hz, 1H), 4.72 (d, J=14.8 Hz, 1H), 4.04 (d, J=14.8 Hz, 1H), 3.88 (dd, J=13.3, 6.7 Hz, 1H), 3.81 (s, 3H), 3.78 (s, 3H), 2.77-2.59 (m, 4H), 2.38-2.21 (m, 3H), 2.10 (dd, J=13.8, 7.8 Hz, 1H), 1.82 (dd, J=13.3, 6.2 Hz, 1H).

Workup

  1. customquenched with saturated aqueous ammonium chloride
  2. extractionThe mixture was then extracted twice with dichloromethane
  3. dry with materialthe combined extracts dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by column chromatography on silica gel (gradient: 0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-393b65e9f52449058d9238ac97ec5a82
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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