Boron trifluoride etherate → 5-Cyclopropyl-1-(phenylmethyl)-2-pyrrolidinone

HRID 2367230Notes

Reaction equation

[CH:1]1([C:4]2(O)[N:8]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7](=[O:16])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH:1]1([CH:4]2[N:8]([CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:7](=[O:16])[CH2:6][CH2:5]2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

To 5-cyclopropyl-5-hydroxy-1-(phenylmethyl)-2-pyrrolidinone (400 mg, 1.73 mmol) in CH2Cl2 (10 mL) at −78° C. was added a mixture of triethylsilane (2.76 mL, 17.3 mmol) and BF3.OEt2 (0.88 mL, 6.92 mmol) dropwise. The resulting reaction mixture was stirred for 2 hours at −78° C., then allowed to warm to room temperature and stirred overnight. The reaction was quenched by adding a saturated aqueous NaHCO3 solution, and the aqueous layer was extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% hexanes to 100% EtOAc) afforded the title compound (240 mg, 65%) as a colorless oil. LC-MS (ES) m/z=216 [M+H]+.

Workup

customThe resulting reaction mixture
temperatureto warm to room temperature
stirringstirred overnight
customThe reaction was quenched
additionby adding a saturated aqueous NaHCO3 solution
extractionthe aqueous layer was extracted with CH2Cl2 (2×)
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-2c38375a8326480389b378a94c88a8f4
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

Loading…