1-(Piperidin-4-yl)pyrrolidin-2-one hydrochloride → 1-(1-{4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}piperidin-4-yl)pyrrolidin-2-one

HRID 272872ノート

反応式

HRID 272872 の反応式
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH:22]=O)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:24]1[CH2:29][N:28]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[C:26](=[O:27])[CH2:25]1.Cl>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3([CH2:22][N:33]4[CH2:34][CH2:35][CH:30]([N:28]5[CH2:29][CH2:24][CH2:25][C:26]5=[O:27])[CH2:31][CH2:32]4)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

5

反応物 2

HCID 230188401-(Piperidin-4-yl)pyrrolidin-2-one hydrochlorideHCID 598374274-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde

生成物 1

HCID 598375351-(1-{4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}piperidin-4-yl)pyrrolidin-2-one収率 22.5%

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 702Ethanol溶媒

実験手順

4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde (400 mg, 1.260 mmol), 4-(N-2-pyrrolidinone)piperidine hydrochloride (493 mg, 4.407 mmol), absolute ethanol (16 ml), activated 3 Å molecular sieves (400 mg), titanium (IV) isopropoxide (1.86 ml, 6.30 mmol) and STAB (2.27 g, 10.71 mmol) were reacted in accordance with the general procedure D. The isolated waxy solid was purified by column chromatography on silica eluting with DCM(95):MeOH(4):NH3(1) to give the title compound as a pale yellow oil (133 mg, 22%). 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.86 (d, 2H), 4.02 (t, 2H), 3.83-3.71 (m, 3H), 3.52 (dt, 2H), 3.32 (t, 2H), 2.63 (t, 2H), 2.53 (br s, 4H), 2.41-2.30 (m, 6H), 2.18 (dt, 2H), 2.12-1.36 (m, 16H).

後処理

  1. customThe isolated waxy solid was purified by column chromatography on silica eluting with DCM(95)

出典と根拠

ORDレコード
ord-ed0b1877131f4c8b958e0953b5023921
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

反応ノート

読み込み中…