Water → HCID 66703510, compound

HRID 1821639Notes

Reaction equation

HRID 1821639 reaction equation
[CH3:1][N:2]([CH:4]([CH:7]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1)[C:5]#N)[CH3:3].[F:17][C:18]1[CH:19]=C([Mg]Br)[CH:21]=[CH:22][CH:23]=1.[Cl-].[NH4+].O>C1COCC1>[O:14]1[C:10]2([CH2:15][CH2:16][CH:7]([CH:4]([N:2]([CH3:3])[CH3:1])[C:5]3[CH:21]=[CH:22][CH:23]=[C:18]([F:17])[CH:19]=3)[CH2:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178505773HCID 178505773, compound

Product 1

HCID 66703510HCID 66703510, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the aminonitrile 12 (23.45 g, 104 mmole) in absolute THF (100 ml) was added dropwise to a 1M solution of 3-fluorophenyl magnesium bromide in THF (208 ml, 208 mmole) under argon and while cooling with ice, and stirred for 20 hours at RT. To work up the reaction mixture saturated ammonium chloride solution (100 ml) and water (100 ml) were added while cooling with ice and the mixture was extracted with diethyl ether (3×100 ml). The organic phase was washed with water and saturated sodium chloride solution, dried and concentrated by evaporation.

Workup

  1. temperaturewhile cooling with ice
  2. additionwere added
  3. temperaturewhile cooling with ice
  4. extractionthe mixture was extracted with diethyl ether (3×100 ml)
  5. washThe organic phase was washed with water and saturated sodium chloride solution
  6. customdried
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ac2eb12069dd494a8f9d0d5c9558ac28
Source dataset
uspto-grants-2009_10
Patent number
US07608619B2

Reaction notes

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