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

HRID 883169노트

반응식

HRID 883169 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-134ac9aab2a8478991f3ce260e0c9359
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236835B2

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