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Triethylamine → [1-(2,4-Dimethoxybenzyl)-3-methyl-5-oxopyrrolidin-3-yl]methyl methanesulfonate

HRID 595214
ノート
印刷プレビュー

反応式

HRID 595214 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:13][O:14][C:15]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:16]=1[CH2:17][N:18]1[CH2:22][C:21]([CH2:24][OH:25])([CH3:23])[CH2:20][C:19]1=[O:26]>C(Cl)Cl.O>[CH3:1][S:2]([O:25][CH2:24][C:21]1([CH3:23])[CH2:20][C:19](=[O:26])[N:18]([CH2:17][C:16]2[CH:27]=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:15]=2[O:14][CH3:13])[CH2:22]1)(=[O:4])=[O:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1317345741-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-4-methylpyrrolidin-2-one

生成物 1

HCID 118208667[1-(2,4-Dimethoxybenzyl)-3-methyl-5-oxopyrrolidin-3-yl]methyl methanesulfonate

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

Methanesulfonyl chloride (305 mg, 2.65 mmol) and triethylamine (540 mg, 5.35 mmol) were added to a solution of 1-(2,4-dimethoxybenzyl)-4-(hydroxymethyl)-4-methylpyrrolidin-2-one (500 mg, 1.75 mmol) in DCM (5 mL) at 0° C. The mixture was stirred at room temperature for 16 hours and then diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether) to give [1-(2,4-dimethoxybenzyl)-3-methyl-5-oxopyrrolidin-3-yl]methyl methanesulfonate. MS ESI calc'd. for C16H24NO6S [M+H]+ 358. found 358. 1H NMR (400 MHz, CDCl3): δ 7.15 (d, J=8.4 Hz, 1H), 6.46-6.44 (m, 2H), 4.41 (s, 2H), 4.02-3.96 (m, 2H), 3.81 (s, 3H), 3.80 (s, 3H), 3.22 (d, J=6.4 Hz, 1H), 2.99-2.95 (m, 4H), 2.41 (d, J=16.8 Hz, 1H), 2.24 (d, J=16.8 Hz, 1H), 1.19 (s, 3H).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-7b5441032e994be9a183dd67b045f3ac
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242984B2

反応ノート

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