1,2-Dichloroethane → (5R)-5-{2-[4-(4-fluorophenyl)-1-piperazinyl]-2-oxoethyl}-2,2-dimethyl-1,3-dioxolan-4-one

HRID 217648Notes

Reaction equation

[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][C:8]([OH:10])=O)[C:4](=[O:11])[O:3]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.Cl.[F:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1>C(Cl)Cl>[F:29][C:30]1[CH:31]=[CH:32][C:33]([N:36]2[CH2:41][CH2:40][N:39]([C:8](=[O:10])[CH2:7][C@H:5]3[O:6][C:2]([CH3:1])([CH3:12])[O:3][C:4]3=[O:11])[CH2:38][CH2:37]2)=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid (3.48 g; 20.0 mmol; 1.0 eq.), TEA (6.07 g; 60.0 mmol; 3.0 eq.) in DCM (60 mL) was added HOBt (2.97 g; 22.0 mmol; 1.1 eq.) and the mixture was chilled to 0° C. EDC (4.6 g; 24.0 mmol; 1.2 eq.) was then added and the resulting reaction mixture was stirred for 15 min at 0° C. 1-(4-fluorophenyl)piperazine dihydrochloride (5.57 g; 22.0 mmol; 1.1 eq.) was added and the resulting reaction mixture was stirred at RT over night. Purification by flash chromatography (AcOEt/c-Hex: 50/50) gave the title compound as a colorless oil (5.12 g, 76%). M+(ESI): 337.2. HPLC (Condition A): Rt: 2.5 min (HPLC purity: 97.4%).

Workup

customthe resulting reaction mixture
customthe resulting reaction mixture
stirringwas stirred at RT over night
customPurification by flash chromatography (AcOEt/c-Hex: 50/50)

Sources & evidence

ORD record: ord-43f0dd96afdc4ff7ab13c4a40f2a9bf3
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198280B2

Reaction notes

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