Water → HCID 54379724, compound

HRID 1196257Notes

Reaction equation

HRID 1196257 reaction equation
[C:1]([NH:9][CH2:10][CH:11]1[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:18][CH2:17][C:12]21[O:16][CH2:15][CH2:14][O:13]2)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([NH:9][CH2:10][CH:11]1[C:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:19][CH2:18][CH2:17][C:12]21[O:13][CH2:14][CH2:15][O:16]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 53757815HCID 53757815, compound

Product 1

HCID 54379724HCID 54379724, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (RS)-6-benzamidomethyl-7,7-diphenyl-1,4-dioxaspiro[4.5]decane (8.1 g) in anhydrous tetrahydrofuran (150 cc) is added dropwise, in the course of 1 hour 30 minutes and while the temperature of the reaction mixture is maintained at +5° C., to a suspension, cooled to +5° C. of lithium aluminum hydride (1.9 g) in anhydrous tetrahydrofuran (60 cc), and the mixture is then brought to reflux for 24 hours. The reaction mixture is then cooled to +5° C., treated with distilled water (2.1 cc), then with 5N aqueous sodium hydroxide solution (1.9 cc) and then with distilled water (5.8 cc), filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel with a slight excess pressure of nitrogen (0.04-0.063 mm, diameter 5 cm, height 29 cm), eluting with ethyl acetate and collecting 120-cc fractions. Fractions 3 to 12 are combined and concentrated to dryness under reduced pressure (2.7 kPa). (RS)-6-Benzylaminomethyl-7,7-diphenyl-1,4-dioxaspiro[4.5]decane (6.6 g) is obtained in the form of a yellow oil.

Workup

  1. temperatureis maintained at +5° C., to a suspension
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction mixture is then cooled to +5° C.
  4. filtrationwith 5N aqueous sodium hydroxide solution (1.9 cc) and then with distilled water (5.8 cc), filtered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is chromatographed on a column of silica gel with a slight excess pressure of nitrogen (0.04-0.063 mm, diameter 5 cm, height 29 cm)
  7. washeluting with ethyl acetate
  8. customcollecting 120-cc fractions
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-e05d1d730edb48d897f300085d8bfdea
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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