Tetrahydrofuran → (8-Benzyl-1,4-dioxaspiro[4,5]dec-8-yl)(4-methoxybenzyl)amine

HRID 2422395Notes

Reaction equation

HRID 2422395 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[N:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.O1CCCC1.[CH2:26]([Mg]Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[NH4+]>O>[CH2:26]([C:8]1([NH:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 67127236(1,4-Dioxaspiro[4,5]dec-8-ylidene)-(4-methoxybenzyl)amineHCID 178418336HCID 178418336, compound

Product 1

HCID 67127336(8-Benzyl-1,4-dioxaspiro[4,5]dec-8-yl)(4-methoxybenzyl)amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a heated flask a 0.6 M solution of (1,4-dioxaspiro[4,5]dec-8-ylidene)-(4-methoxybenzyl)amine in tetrahydrofuran (17 ml, 10 mmol) was added slowly dropwise under argon and with ice cooling to a 2 M solution of benzyl magnesium chloride in tetrahydrofuran (10 ml, 20 mmol). The mixture was stirred for 20 h at room temperature and then added dropwise to 20% ammonium chloride solution (20 ml) with iced water cooling. The organic phase was separated off and the aqueous phase was extracted with diethyl ether (3×20 ml). The combined organic phases were washed with 2 N sodium hydroxide solution (20 ml) and water (20 ml), dried with sodium sulfate and concentrated to small volume under vacuum. The crude product (3.7 g) was purified by flash chromatography (370 g, 22×7.5 cm) with ethyl acetate/cyclohexane (1:2) with 1% triethylamine. Yield: 1.27 g (34%), yellowish oil.

Workup

  1. customThe organic phase was separated off
  2. extractionthe aqueous phase was extracted with diethyl ether (3×20 ml)
  3. washThe combined organic phases were washed with 2 N sodium hydroxide solution (20 ml) and water (20 ml)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated to small volume under vacuum
  6. customThe crude product (3.7 g) was purified by flash chromatography (370 g, 22×7.5 cm) with ethyl acetate/cyclohexane (1:2) with 1% triethylamine

Sources & evidence

ORD record
ord-e351d33a730b4a09ab69e650ed646fa5
Source dataset
uspto-grants-2011_06
Patent number
US07960404B2

Reaction notes

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