Rolziracetam → 5-[4-(3-Fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one

反応式

[CH2:1]1[CH:8]2[N:4]([C:5](=[O:9])[CH2:6][CH2:7]2)[C:3](=[O:10])[CH2:2]1.[F:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[CH2:15][Mg]Cl>>[F:11][C:12]1[CH:13]=[C:14]([CH2:15][C:5](=[O:9])[CH2:6][CH2:7][CH:8]2[NH:4][C:3](=[O:10])[CH2:2][CH2:1]2)[CH:18]=[CH:19][CH:20]=1

参加物

反応物 2

HCID 71893Rolziracetam

HCID 178505696HCID 178505696、化合物

生成物 1

HCID 129700935-[4-(3-Fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one収率 62.3%

実験手順

Analogous to the procedure described for Example 1A, Step A, tetrahydro-pyrrolizine-3,5-dione (2 g, 14 mmol) was reacted with 3-fluorobenzylmagnesium chloride (0.25M in Et2O, 62 mL, 15.5 mmol) over 2.5 h. Purification by medium pressure chromatography using a solvent gradient (1:1 hexanes:EtOAc to 2:1 EtOAc:hexanes to EtOAc to 2% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2) provided 5-[4-(3-fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one (2.1730 g). 1H NMR (CDCl3) δ7.32–7.27 (m, 1H), 7.00–6.90 (m, 3H), 6.12 (bs, 1H), 3.69 (s, 2H), 3.59 (m, 1H), 2.52 (t, 2H), 2.30 (m, 2H), 2.19 (m, 1H), 1.75 (m, 2H), 1.65 (m, 1H).

後処理

customPurification by medium pressure chromatography

出典と根拠

ORDレコード: ord-7de30eec33ab40ccb00c28497a2d2dd9
出典データセット: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07192979B2

反応ノート

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