Pyridine → (R)-2-oxo-3-(tetrahydrofuran-3-yl)imidazolidine-1-carbonyl chloride

HRID 2278953Notes

Reaction equation

[C:1]([Cl:4])(Cl)=[O:2].[O:5]1[CH2:9][CH2:8][C@@H:7]([N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:6]1.N1C=CC=CC=1>C(Cl)Cl>[O:15]=[C:11]1[N:10]([C@@H:7]2[CH2:8][CH2:9][O:5][CH2:6]2)[CH2:14][CH2:13][N:12]1[C:1]([Cl:4])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A 0° C. solution of phosgene (20% in toluene, 1.132 mL, 2.151 mmol) in DCM (9 mL) was treated slowly with a solution of (R)-1-(tetrahydrofuran-3-yl)imidazolidin-2-one (0.28 g, 1.793 mmol) and pyridine (0.290 mL, 3.59 mmol) in DCM (9 mL) and stirred at 0° C. for 45 min. The mixture was concentrated to dryness to afford crude (R)-2-oxo-3-(tetrahydrofuran-3-yl)imidazolidine-1-carbonyl chloride (100% yield assumed) which was used without further purification.

Workup

concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record: ord-9466a1c56b04484490bc8e76f6071ba0
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133183B2

Reaction notes

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