Ammonium Chloride → HCID 67127510, compound

HRID 2422397Notes

Reaction equation

HRID 2422397 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.[F:17][C:18]1[CH:19]=C([Mg]Br)[CH:21]=[CH:22][CH:23]=1.[Cl-].[NH4+]>O1CCCC1>[F:17][C:18]1[CH:19]=[C:15]([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:23]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 57475115HCID 57475115, compoundHCID 178505773HCID 178505773, compound

Product 1

HCID 67127510HCID 67127510, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8-azetidin-1-yl-1,4-dioxaspiro[4,5]decane-8-carbonitrile (13.9 g, 62.53 mmol) in anhydrous tetrahydrofuran (70 ml) was added dropwise under argon and with ice cooling to a 1M solution of 3-fluorophenyl magnesium bromide in tetrahydrofuran (250 ml, 250 mmol) and then the mixture was stirred for 24 h at room temperature. Then saturated ammonium chloride solution (150 ml) was added with ice cooling and the mixture was stirred vigorously for 20 min. The phases were then 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 obtained in this way in a yield of 18 g (99%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred vigorously for 20 min
  2. customThe phases were then separated
  3. extractionthe aqueous phase was extracted with diethyl ether (3×50 ml)
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-d562c0d70bb946359443be627932a54a
Source dataset
uspto-grants-2011_06
Patent number
US07960404B2

Reaction notes

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