Sodium Hydroxide → 1-(1,4-Dioxa-spiro[4.5]dec-8-yl)-1-phenyl-ethylamine

HRID 45201

Reaction equation

HRID 45201 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:9]1[C:13]2([CH2:18][CH2:17][CH:16]([C:19]#[N:20])[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1.[CH3:21][Li].[OH-].[Na+]>C(OCC)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[O:9]1[C:13]2([CH2:18][CH2:17][CH:16]([C:19]([NH2:20])([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH3:21])[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 111164331,4-Dioxaspiro[4.5]decane-8-carbonitrileHCID 178418255HCID 178418255, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 583810151-(1,4-Dioxa-spiro[4.5]dec-8-yl)-1-phenyl-ethylamine

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Under argon, phenylmagnesium bromide (3M) in diethyl ether (6.7 mL, 20 mmol) was added to a solution of 1,4-dioxa-spiro[4.5]decane-8-carbonitrile (3.34 g, 20 mmol) in diethyl ether (60 mL). The mixture was stirred for 30 minutes. Titanium (IV) isopropoxide (5.7 g, 20 mmol) was then added. After stirring for 5 min, methyl lithium (1.6 M in diethyl ether, 31.2 mL, 50 mmol) was added and the reaction was heated under reflux for 10 hours. After cooling in ice/water the brown mixture was treated cautiously with 2M NaOH solution (30 mL) dropwise (exothermic). The mixture was extracted with t-butyl methyl ether and dried over sodium sulphate. After filtration the organic phase was evaporated to give 5 g of a pale yellow oil, which was used in the next step without further purification. Rt=2.10 min (Method 2). Detected mass: 261.2 (M+H+).

Workup

  1. stirringAfter stirring for 5 min
  2. temperaturethe reaction was heated
  3. temperatureunder reflux for 10 hours
  4. extractionThe mixture was extracted with t-butyl methyl ether
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration the organic phase
  7. customwas evaporated

Sources & evidence

ORD record
ord-7306a45cd4c24805a47794cf7597b8ed
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Linked notes

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