Water → HCID 66701322, compound

HRID 876233Notes

Reaction equation

HRID 876233 reaction equation
B(Br)(Br)Br.[CH2:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH:17]([O:19]C)[CH2:16][N:15]([C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])[CH2:14]2)=[CH:9][CH:8]=1)[CH3:6].C(=O)(O)[O-].[Na+].O>ClCCl>[CH2:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:14][N:15]([C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])[CH2:16][CH:17]([OH:19])[CH2:18]2)=[CH:9][CH:8]=1)[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 66701280HCID 66701280, compound

Product 1

HCID 66701322HCID 66701322, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon and at 0° C., 4.6 ml of a boron tribromide solution (1 molar in dichloromethane, 4.6 mmol, 2 eq.) were added to a solution of 890 mg (2.3 mmol) of 4-{[3-(4-ethylphenyl)-5-methoxypiperidin-1-yl]carbonyl}morpholine in 22 ml of dichloromethane. The reaction mixture was stirred at RT for 2 h, then poured onto ice, neutralized with solid sodium bicarbonate and, after addition of water and phase separation, extracted three times with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product was then purified by preparative HPLC (Reprosil C18, water with 0.1% trifluoroacetic acid/acetonitrile gradient). Yield: 314 mg (43% of theory)

Workup

  1. additionpoured onto ice
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was then purified by preparative HPLC (Reprosil C18, water with 0.1% trifluoroacetic acid/acetonitrile gradient)

Sources & evidence

ORD record
ord-2c25fc13202e40478d72cfd02f7f377d
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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