Aluminum(III) Chloride → 1-(1,4-Dioxaspiro[4.5]dec-7ylmethyl)-1,2,3,6-tetrahydro-4-phenylpyridine

HRID 1654690Notes

Reaction equation

HRID 1654690 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:11]1[C:15]2([CH2:20][CH2:19][CH2:18][CH:17]([C:21]([N:23]3[CH2:28][CH:27]=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:25][CH2:24]3)=O)[CH2:16]2)[O:14][CH2:13][CH2:12]1>C(OCC)C.O1CCCC1>[O:14]1[C:15]2([CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][N:23]3[CH2:24][CH:25]=[C:26]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:27][CH2:28]3)[CH2:16]2)[O:11][CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 103590941-(1,4-Dioxaspiro[4.5]dec-7-yl carbonyl)-1,2,3,6-tetrahydro-4-phenylpyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 102450751-(1,4-Dioxaspiro[4.5]dec-7ylmethyl)-1,2,3,6-tetrahydro-4-phenylpyridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of aluminum chloride (14.54 g) in 500 mL of anhydrous diethyl ether is added dropwise to a suspension of lithium aluminum hydride (12.41 g) in 500 mL of tetrahydrofuran. The mixture is stirred at room temperature for 30 minutes. A solution of 1-(1,4-dioxaspiro[4.5]dec-7-yl carbonyl)-1,2,3,6-tetrahydro-4-phenylpyridine (Step B) in 500 mL of tetrahydrofuran is added dropwise. The mixture is stirred at room temperature overnight, and it is quenched by careful addition of 13 mL of water, followed by 59 mL of 25% aqueous sodium hydroxide solution. The resulting mixture is stirred at room temperature for 2 hours, filtered through celite, and concentrated in vacuo. The title compound is obtained (90.40 g) as a light yellow oil (silica; Rf =0.2; 1% methanol, 99% chloroform).

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. customit is quenched by careful addition of 13 mL of water
  3. stirringThe resulting mixture is stirred at room temperature for 2 hours
  4. filtrationfiltered through celite
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33013ae522f94826b94c2ea94aacce37
Source dataset
uspto-grants-1995_04
Patent number
US05409931

Reaction notes

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