3,3-Difluoropyrrolidine hydrochloride → HCID 59583481, compound

HRID 219464Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])=[C:9]([O:23][CH3:24])[C:8]([Cl:25])=[C:7]([CH3:26])[C:6]=1[C:27](=[O:29])[CH3:28].Cl.[F:31][C:32]1([F:37])[CH2:36][CH2:35][NH:34][CH2:33]1>>[Cl:25][C:8]1[C:7]([CH3:26])=[C:6]([C:27](=[O:29])[CH3:28])[C:5]([O:4][CH2:3][CH2:2][N:34]2[CH2:35][CH2:36][C:32]([F:37])([F:31])[CH2:33]2)=[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[C:9]=1[O:23][CH3:24]

Participants

Reactant 2

HCID 249034823,3-Difluoropyrrolidine hydrochloride

HCID 595835231-{2-(2-Bromo-ethoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

Product 1

HCID 59583481HCID 59583481, compoundYield 54%

Procedure

Example 8a (83 mg, 0.17 mmol) was reacted with 3,3-difluoropyrrolidine hydrochloride (2.5 eq.) as described under General Procedure K and the crude mixture was purified by flash chromatography (silica gel, hexane/Et2O 70:30) to afford the title compound as a pale yellow oil (47 mg, 54%). 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 7.01-6.95 (m, 2H), 4.03 (t, J=5.6 Hz, 2H), 3.95 (dt, J=2.1, 6.8 Hz, 2H), 3.83 (s, 3H), 2.97 (m, 1H), 2.95 (t, J=13.4 Hz, 2H), 2.79-2.71 (m, 4H), 2.49 (s, 3H), 2.33-2.21 (m, 2H), 2.18 (s, 3H), 2.06-1.98 (m, 2H), 1.30 (d, J=6.9 Hz, 3H). MS (ES+) m/z 514.2 (M+H+).

Workup

customthe crude mixture was purified by flash chromatography (silica gel, hexane/Et2O 70:30)

Sources & evidence

ORD record: ord-ddba689e68ed48ccb24be7d08f69eb91
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202513B2

Reaction notes

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