Tetrahydrofuran → HCID 66703510, compound

HRID 557515Notes

Reaction equation

HRID 557515 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].C1COCC1.[F:22][C:23]1[CH:24]=C([Mg]Br)[CH:26]=[CH:27][CH:28]=1.[Cl-].[NH4+]>C(OCC)C.O>[O:14]1[C:10]2([CH2:15][CH2:16][CH:7]([CH:4]([N:2]([CH3:3])[CH3:1])[C:5]3[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=3)[CH2:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178505773HCID 178505773, compound

Product 1

HCID 66703510HCID 66703510, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of the aminonitrile 3 (23.45 g, 104 mmol) in abs. THF (100 ml) was added dropwise, under argon and while cooling with ice, to a 1M solution of 3-fluorophenylmagnesium bromide in THF (208 ml, 208 mmol), and stirring was carried out for 20 h at RT. For working up the reaction mixture, saturated ammonium chloride solution (100 ml) and water (100 ml) were added, while cooling with ice, and extraction with diethyl ether (3×100 ml) was carried out. The organic phase was washed with water and saturated sodium chloride solution, dried and concentrated.

Workup

  1. additionwere added
  2. washThe organic phase was washed with water and saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ca1823e95eee487dae330614f6da0c26
Source dataset
uspto-grants-2011_11
Patent number
US08058475B2

Reaction notes

Loading…