Sodium hydride → (R)-1-(tetrahydrofuran-3-yl)imidazolidin-2-one

HRID 2278952Notes

Reaction equation

HRID 2278952 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C@@H:8]1[CH2:12][CH2:11][O:10][CH2:9]1)=[O:6].[H-].[Na+]>C1COCC1>[O:10]1[CH2:11][CH2:12][C@@H:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[CH2:9]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 90426389(R)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea

Product 1

HCID 90427282(R)-1-(tetrahydrofuran-3-yl)imidazolidin-2-oneYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A −20° C. solution of (R)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea (0.522 g, 2.71 mmol) in THF (30 mL) was treated with NaH (60% in mineral oil, 0.130 g, 3.25 mmol) and the mixture stirred at RT overnight as the cooling bath expired. The mixture was treated with satd. NH4Cl, dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford (R)-1-(tetrahydrofuran-3-yl)imidazolidin-2-one (280 mg, 66%). MS (ESI) m/z: 157.1 (M+H+).

Workup

  1. additionThe mixture was treated with satd
  2. dry with materialNH4Cl, dried over MgSO4
  3. concentrationconcentrated to dryness
  4. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-4715afd095904ffaa2594630c613c78a
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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