Triethylamine → 3,3-Difluoro-1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidine

HRID 1181356Notes

Reaction equation

[F:1][C:2]1([F:7])[CH2:6][CH2:5][NH:4][CH2:3]1.Br[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[O:21][CH3:22].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1([F:7])[CH2:6][CH2:5][N:4]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[O:21][CH3:22])[CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

3,3-Difluoropyrrolidine (0.4589 g, 2.0859 mmol) and 1-(2-bromoethoxy)-2-methoxy-4-nitrobenzene (0.5757 g, 2.0859 mmol) were combined in DMF (5 mL). Triethylamine (0.6332 g, 6.2577 mmol) was added. The reaction was heated to 80° C. and stirred for 18 h. The reaction was cooled to RT and diluted with EtOAc (50 mL). The organics were washed with water (3×100 mL), dried over MgSO4, filtered and concentrated. The residue was purified by chromatatron (1:1 Hex:EtOAc) to give 0.173 g (0.5728 mmol, 27%) of the product as a light yellow oil. 1H NMR (CDCl3) δ 7.90 (d, 1H, 9 Hz), 7.75 (s, 1H), 6.89 (d, 1H, J=9 Hz), 4.21 (t, 2H, J=5.6 Hz), 3.94 (s, 3H), 3.07 (t, 2H, J=13.3 Hz), 2.99 (t, 2H, J=5.7 Hz), 2.89 (t, 2H, J=7.1 Hz), 2.28 (m, 2H).

Workup

temperatureThe reaction was cooled to RT
washThe organics were washed with water (3×100 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatatron (1:1 Hex:EtOAc)

Sources & evidence

ORD record: ord-3618868d739042d9a0f576c9277cc79b
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285557B2

Reaction notes

Loading…