Sodium hydride → HCID 90427717, compound

HRID 2278937Notes

Reaction equation

HRID 2278937 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 90426387HCID 90426387, compound

Product 1

HCID 90427717HCID 90427717, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A −20° C. solution of (S)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea (0.11 g, 0.571 mmol) in THF (6 mL) was treated with NaH (60% in mineral oil, 0.057 g, 1.428 mmol), stirred at −20° C. for 0.5 h, then at RT for 1 h. The mixture was treated with satd. NH4Cl and H2O, extracted with EtOAc (3×) and THF (2×) and the combined organics were washed with brine (1×), dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford (S)-1-(tetrahydrofuran-3-yl)imidazolidin-2-one (26 mg, 29%). 1H NMR (400 MHz, DMSO-d6): δ 6.32 (brs, 1 H), 4.36-4.30 (m, 1 H), 3.83-3.77 (m, 1 H), 3.63-3.53 (m, 4 H), 3.31-3.26 (m, 1 H), 3.24-3.21 (m, 2 H); 2.05-1.96 (m, 1 H); 1.84-1.76 (m, 1 H). MS (ESI) m/z: 157.1 (M+H+).

Workup

  1. waitat RT for 1 h
  2. additionThe mixture was treated with satd
  3. extractionNH4Cl and H2O, extracted with EtOAc (3×) and THF (2×)
  4. washthe combined organics were washed with brine (1×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness
  7. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-70661dde5eaf4e0a8ee8d04435a1ddaa
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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