Water → HCID 44252103, compound

HRID 2063736Notes

Reaction equation

HRID 2063736 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[CH2:10][CH:11]([CH:13]1[CH2:18][CH2:17][C:16]([N:21]([CH3:23])[CH3:22])([C:19]#N)[CH2:15][CH2:14]1)[OH:12].[C:24]1([Mg]Cl)[CH:29]=[CH:28]C=[CH:26][CH:25]=1.[Cl-].[NH4+].O>O1CCCC1>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][N:2]1[CH2:10][CH:11]([CH:13]1[CH2:18][CH2:17][C:16]([N:21]([CH3:23])[CH3:22])([C:19]2[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=2)[CH2:15][CH2:14]1)[OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 66887153HCID 66887153, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 44252103HCID 44252103, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-[2-(1,3-dihydroisoindol-2-yl)-1-hydroxyethyl]-1-dimethylaminocyclohexanecarbonitrile (666 mg, 2.12 mmol) in anhydrous tetrahydrofuran (30 ml) was added dropwise to a 2 M solution of phenylmagnesium chloride in tetrahydrofuran (4.25 ml, 8.49 mmol), while cooling with ice, and the mixture was stirred at room temperature overnight. Saturated ammonium chloride solution and water (10 ml of each) were then added dropwise to the mixture, while cooling with ice. The tetrahydrofuran was distilled off in vacuo and the residue was extracted with diethyl ether (3×30 ml). The combined organic phases were dried with sodium sulfate and concentrated in vacuo. The crude product (761 mg) was purified by flash chromatography with chloroform/methanol (9:1). Renewed flash chromatography with chloroform (saturated with 25% aqueous ammonia solution)/methanol (95:5) gave a yield of 83 mg (10%) of beige-coloured solid.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. distillationThe tetrahydrofuran was distilled off in vacuo
  4. extractionthe residue was extracted with diethyl ether (3×30 ml)
  5. dry with materialThe combined organic phases were dried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product (761 mg) was purified by flash chromatography with chloroform/methanol (9:1)

Sources & evidence

ORD record
ord-f7c0eaf55b0f49e2b756ece71414144b
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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