Water → HCID 10049412, compound

HRID 1975075Notes

Reaction equation

HRID 1975075 reaction equation
[H-].[Na+].[Br:3][C:4]1[S:12][C:11]2[C@@H:10]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3=[O:19])[C@H:9]([OH:20])[C:8]([CH3:22])([CH3:21])[O:7][C:6]=2[CH:5]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C=O)C>[CH2:23]([O:20][C@@H:9]1[C:8]([CH3:22])([CH3:21])[O:7][C:6]2[CH:5]=[C:4]([Br:3])[S:12][C:11]=2[C@H:10]1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:19])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10067049HCID 10067049, compound

Product 1

HCID 10049412HCID 10049412, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 0.47 g, 11.7 mmol) was added to a solution of trans-2-bromo-5,6-dihydro-6-hydroxy-5,5-dimethyl-7-(2-oxopiperidin-1-yl)-7H-thieno-[3,2-b]pyran (4.0 g, 11.1 mmol) in DMF (50 mL) at 0° C. and stirred at rt for 30 min. Benzylbromide (1.45 mL, 12.2 mmol) was added to the resultant solution and stirred at rt for 2 h. The solution was poured into water (200 mL) and extracted into dichloromethane. The organic phase was washed several times with water and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography using 2% methanol in dichloromethane as the eluant. The product was recrystallized from dichloromethane/hexane to give a colorless solid, 3.87 g (77%); mp 146°-147° C.; IR(KBr): 1634 and 1570 cm-1 ; MS: m/z 450 (MH+); 1H NMR(CDCl 3): 1.32 (s, 3H), 1.50 (s, 3H), 1.53-1.77 (m, 4H), 2.37-2.45 (m, 2H), 2.87 (m, 1H), 3.08 (m, 1H), 3.69 (d, J=8.6 Hz, 1H), 4.60 (d, J=11.8 Hz, 1H), 4.73 (d, J=11.8 Hz, 1H), 5.90 (bs, 1H), 6.54 (s, 1H) and 7.26-7.37 (m, 5H).

Workup

  1. stirringstirred at rt for 2 h
  2. extractionextracted into dichloromethane
  3. washThe organic phase was washed several times with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by flash chromatography
  7. customThe product was recrystallized from dichloromethane/hexane
  8. customto give a colorless solid, 3.87 g (77%)

Sources & evidence

ORD record
ord-abda0f8356f04e1b982e21c5bf290e02
Source dataset
uspto-grants-1994_02
Patent number
US05284857

Reaction notes

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