Tetrahydrofuran → [(1,4-Dioxa-spiro[4.5]dec-8-yl)-4-fluorophenylmethyl]-dimethylamine

HRID 557514Notes

Reaction equation

HRID 557514 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:28]=[CH:27]C([Mg]Br)=[CH:25][CH:24]=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:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=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 178418676HCID 178418676, compound

Product 1

HCID 66703550[(1,4-Dioxa-spiro[4.5]dec-8-yl)-4-fluorophenylmethyl]-dimethylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of the aminonitrile 3 (19.89 g, 88 mmol) in abs. THF (160 ml) was added dropwise, under argon and while cooling with ice, to a 1M solution of 4-fluorophenylmagnesium bromide in THF (220 ml, 220 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 (Na2SO4) and concentrated.

Workup

  1. additionwere added
  2. washThe organic phase was washed with water and saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7c2ddd5b1c0547f89aca1722448ccad1
Source dataset
uspto-grants-2011_11
Patent number
US08058475B2

Reaction notes

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