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

HRID 883169Notes

Reaction equation

HRID 883169 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-134ac9aab2a8478991f3ce260e0c9359
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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