3,4-dihydro-2H-pyran → (4S)-4-(2-oxotetrahydro-2H-pyran-4-yloxy)pyrrolidin-2-one

HRID 883169ノート

反応式

HRID 883169 の反応式
[OH:1][C@@H:2]1[CH2:6][NH:5][C:4](=[O:7])[CH2:3]1.[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.C1(C)C=CC(S([O-])(=O)=[O:21])=CC=1.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[O:21]=[C:13]1[CH2:12][CH:11]([O:1][C@@H:2]2[CH2:6][NH:5][C:4](=[O:7])[CH2:3]2)[CH2:10][CH2:9][O:8]1

参加物

6

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 1550842-Pyrrolidinone, 4-hydroxy-, (4S)-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

生成物 1

HCID 68495162(4S)-4-(2-oxotetrahydro-2H-pyran-4-yloxy)pyrrolidin-2-one収率 608.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-4-hydroxypyrrolidin-2-one (1.00 g, 9.89 mmol) in anhydrous dichloromethane (40 mL) was added 3,4-dihydro-2H-pyrane (1.35 mL, 14.84 mmol) and pyridinium p-toluenesulfonate (0.25 g, 0.99 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with diethyl ether (100 mL) and washed with brine (25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford (4S)-4-(2-oxotetrahydro-2H-pyran-4-yloxy)pyrrolidin-2-one as a clear oil (1.20 g, 61%): 1H NMR (300 MHz, CDCl3) δ 6.60 (br s, 1H), 4.98-4.57 (m, 1H), 4.57-4.46 (m, 1H), 3.89-3.70 (m, 1H), 3.68-3.22 (m, 3H), 2.69-2.22 (m, 2H), 1.89-1.50 (m, 6H).

後処理

  1. washwashed with brine (25 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-134ac9aab2a8478991f3ce260e0c9359
出典データセット
uspto-grants-2012_08
特許番号
US08236835B2

反応ノート

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