Water → HCID 57475116, compound

HRID 2422389Notes

Reaction equation

HRID 2422389 reaction equation
[N:1]1([C:5]2([C:15]#N)[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[C:17]1([Mg]Cl)[CH:22]=[CH:21]C=[CH:19][CH:18]=1.[Cl-].[NH4+].O>O1CCCC1>[C:15]1([C:5]2([N:1]3[CH2:4][CH2:3][CH2:2]3)[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 57475115HCID 57475115, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 57475116HCID 57475116, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8-azetidin-1-yl-1,4-dioxaspiro[4,5]decane-8-carbonitrile (2.20 g, 9.9 mmol) in anhydrous tetrahydrofuran (25 ml) was added dropwise under argon and with ice cooling to a 2 M solution of phenyl magnesium chloride in tetrahydrofuran (12 ml, 24 mmol) and then the mixture was stirred overnight at room temperature. After adding saturated ammonium chloride solution (5 ml) and water (5 ml) the phases were separated and the aqueous phase was extracted with diethyl ether (3×50 ml). The combined organic phases were dried with sodium sulfate and concentrated to small volume under vacuum. The crude product was purified by flash chromatography (100 g, 20×4.0 cm) with ethyl acetate/cyclohexane (1:1). Yield: 670 mg (25%), colorless oil.

Workup

  1. customwere separated
  2. extractionthe aqueous phase was extracted with diethyl ether (3×50 ml)
  3. dry with materialThe combined organic phases were dried with sodium sulfate
  4. concentrationconcentrated to small volume under vacuum
  5. customThe crude product was purified by flash chromatography (100 g, 20×4.0 cm) with ethyl acetate/cyclohexane (1:1)

Sources & evidence

ORD record
ord-a63e9bd376e740e5b0e085c8e7514b15
Source dataset
uspto-grants-2011_06
Patent number
US07960404B2

Reaction notes

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