Sodium hydride → HCID 53754471, compound

Temperature

0 °C

A −20° C. solution of 1-(2-chloroethyl)-3-cyclopentylurea (8.5 g, 44.6 mmol) in THF (446 mL), under Ar, was treated with NaH (60% in mineral oil, 4.46 g, 111 mmol), stirred at −10° C. for 1 h, 0° C. for 1 h, then RT for 3 h. The mixture was cooled to 0° C., treated with 50% satd. NH4Cl, the layers separated and the aqueous layer extracted with EtOAc (3×). The combined organics were dried over Na2SO4 and concentrated to dryness. The material was suspended in Et2O, the solids removed via filtration and the filtrate concentrated to dryness. The resulting material was dissolved in DCM, treated drop-wise with hexane until solids formed and the solids were collected via filtration and dried to afford 1-cyclopentylimidazolidin-2-one (4.3 g, 63%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.16 (s, 1 H), 4.07-3.98 (m, 1 H), 3.28-3.22 (m, 2 H), 3.19-3.14 (m, 2 H), 1.66-1.55 (m, 4 H), 1.52-1.41 (m, 4 H); MS (ESI) m/z: 155.1 (M+H+).

1. waitRT for 3 h
2. temperatureThe mixture was cooled to 0° C.
3. additiontreated with 50%
4. customNH4Cl, the layers separated
5. extractionthe aqueous layer extracted with EtOAc (3×)
6. dry with materialThe combined organics were dried over Na2SO4
7. concentrationconcentrated to dryness
8. customthe solids removed via filtration
9. concentrationthe filtrate concentrated to dryness
10. dissolutionThe resulting material was dissolved in DCM
11. additiontreated drop-wise with hexane until solids
12. customformed
13. filtrationthe solids were collected via filtration
14. customdried

ORD record

ord-5211db6bbc3c4c8ead4d4db15bb058a4

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133183B2