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

HRID 352582

반응식

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

참가 물질

반응물 2

HCID 71893Rolziracetam

HCID 178478996HCID 178478996, 화합물

생성물 1

HCID 129700905-[4-(3-Chloro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one수율 51.5%

실험 절차

Analogous to the procedure described for Example 1A, Step A, tetrahydro-pyrrolizine-3,5-dione (2 g, 14 mmol) was reacted with 3-chlorobenzylmagnesium chloride (0.25M in Et2O, 62 mL, 15.5 mmol) over 2 h. Purification by medium pressure chromatography eluting with a solvent gradient (2:1 hexanes:EtOAc to EtOAc to 5% MeOH in CH2Cl2) provided 5-[4-(3-chloro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one (1.9142 g). 1H NMR (CDCl3) δ7.27 (m, 2H), 7.19 (m, 1H), 7.08 (m, 1H), 6.27 (br, 1H), 3.68 (s, 2H), 3.60 (m, 1H), 2.52 (t, 2H), 2.29 (m, 2H), 2.21 (m, 1H), 1.88-1.60 (m, 3H); MS 266.2 (M+1), 264.2 (M−1).

후처리

customPurification by medium pressure chromatography
washeluting with a solvent gradient (2:1 hexanes:EtOAc to EtOAc to 5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록: ord-89253fb86b83492b8704725585a09c31
출처 데이터셋: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06747054B2

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