Sodium Hydroxide → HCID 18507126, compound

HRID 1355573Notes

Reaction equation

HRID 1355573 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[CH2:19][NH:18][C:17](=O)[CH2:16][O:15]2)=[CH:10][CH:9]=1.[OH-].[Na+]>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[O:15][CH2:16][CH2:17][NH:18][CH2:19]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18507160HCID 18507160, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18507126HCID 18507126, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of LAH in THF (1M, 13.9 mL) at 0° C. was added a solution of 6-(4-bromo-phenyl)-6-(3-methoxy-phenyl)-morpholin-3-one (3.34 g, 9.23 mmol) in THF (15 mL). The reaction mixture was stirred at 0° C. for 1 h and at room temperature for 16 h. To the mixture was added H20 (6.2 mL) followed by addition of 15% aqueous NaOH (6.2 mL) and H20 (7 mL). The mixture was filtered through celite and the celite was washed with EtOAc (50 mL). The filtrate was dried over MgSO4 and concentrated to afford 2.82 g of 2-(4-bromophenyl)-2-(3-methoxy-phenyl)-morpholine. 1HNMR (400 MHz, CDCl3) δ 7.43-7.36 (comp, 2H), 7.33-7.20 (comp, 3H), 6.98-6.82 (comp, 2H), 6.79-6.75 (m, 1 H), 3.76 (s, 3H), 3.68-3.69 (comp, 2H), 3.45-3.29 (comp, 2H), 2.93-2.88 (comp, 2H); MS (M+1) 348.01, 350.0.

Workup

  1. additionTo the mixture was added H20 (6.2 mL)
  2. filtrationThe mixture was filtered through celite
  3. washthe celite was washed with EtOAc (50 mL)
  4. dry with materialThe filtrate was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac21d4918211457caebc38111358d5c0
Source dataset
uspto-grants-2003_07
Patent number
US06586431B1

Reaction notes

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