Sodium Hydroxide → HCID 18507133, compound

HRID 1633544Notes

Reaction equation

HRID 1633544 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[Si]([C:22]#[N:23])(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(Cl)Cl.C1COCC1.O>[NH2:23][CH2:22][C:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[OH:9]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 27570324-Bromo-3'-methoxybenzophenoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 18507133HCID 18507133, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (4-bromo-phenyl)-(3-methoxy-phenyl)-methanone (2.06 g, 7.07 mmol), in CH2Cl2 (3.5 mL) at room temperature was added Znl2 (0.15 , 0.47 mmol) followed by addition of TMSCN (4.29 mL, 32.2 mmol). The reaction mixture was stirred at room temperature for 3 h and was quenched by addition of brine (20 mL). The aqueous layer was washed with CH2Cl2 (3×30 mL) and the combined organic extracts were dried over Na2SO4 and concentrated to afford an oil. The resulting oil was dissolved in THF (7 mL) and the solution was added dropwise to a solution of lithium aluminum hydride (LAH) in THF (1M, 8.13 mL) at 0° C. The mixture was stirred at 0° C. for 1 h and at room temperature for 1 h. To the solution was added H2O (1.5 mL) followed by addition of 15% aqueous sodium hydroxide (NaOH) (1.5 mL) and H2O (4.5 mL). The mixture was filtered trough celite and the celite was washed with EtOAc (20 mL). The filtrate was dried over MgSO4 vand concentrated. Purification by flash chromatography with CH2Cl2/MeOH (20:1) afforded 2.1 g of 2-amino-1-(4-bromo-phenyl)-1-(3-methoxy-phenyl)-ethanol. 1HNMR (400 MHz, CDCl3) δ 7.44-7.40 (comp, 2H), 7.33-7.26 (comp, 2H), 7.24-7.20 (m, 1H), 7.01-6.99 (m, 1H), 6.97-6.94 (m, 1H), 3.77 (s, 3H), 3.47-3-35 (comp, 2H), 3.29-3.24 (comp, 2H); MS (M+1) 304.1, 306.1.

Workup

  1. customwas quenched by addition of brine (20 mL)
  2. washThe aqueous layer was washed with CH2Cl2 (3×30 mL)
  3. dry with materialthe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated
  5. customto afford an oil
  6. stirringThe mixture was stirred at 0° C. for 1 h and at room temperature for 1 h
  7. filtrationThe mixture was filtered trough celite
  8. washthe celite was washed with EtOAc (20 mL)
  9. dry with materialThe filtrate was dried over MgSO4
  10. concentrationvand concentrated
  11. customPurification by flash chromatography with CH2Cl2/MeOH (20:1)

Sources & evidence

ORD record
ord-c11cd5d026e644cc83beb96ea058b44b
Source dataset
uspto-grants-2003_01
Patent number
US06503905B1

Reaction notes

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