Water → HCID 54370231, compound

HRID 1196259Notes

Reaction equation

HRID 1196259 reaction equation
[N+:1]([CH2:4][CH:5]1[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][CH2:11][C:6]21[O:10][CH2:9][CH2:8][O:7]2)([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH2:1][CH2:4][CH:5]1[C:14]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:13][CH2:12][CH2:11][C:6]21[O:7][CH2:8][CH2:9][O:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54367906HCID 54367906, compound

Product 1

HCID 54370231HCID 54370231, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (RS)-6-nitromethyl-7,7-diphenyl-1,4-dioxaspiro[4.5]decane (63 g) in anhydrous tetrahydrofuran (300 cc) is added dropwise in the course of 1 hour to a suspension, cooled to +5° C., of lithium aluminium hydride (8.13 g) in anhydrous tetrahydrofuran (250 cc) while the temperature of the reaction mixture is maintained at +5° C., and the mixture is then brought to reflux for 2 hours. The reaction mixture is then cooled to +5° C., treated with distilled water (8.93 cc), then with 5N aqueous sodium hydroxide solution (8 cc) and then with distilled water (25 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 6.5 cm, height 45 cm), eluting with a mixture of dichloromethane and methanol (90:10) by volume) and collecting 120-cc fractions. Fractions 10 to 31 are combined and concentrated to dryness under reduced pressure (2.7 kPa). (RS)-6-Aminomethyl-7,7-diphenyl-1,4-dioxaspiro[4.5]decane (16.5 g) is obtained in the form of an orange-colored oil.

Workup

  1. temperatureis maintained at +5° C.
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction mixture is then cooled to +5° C.
  4. filtrationwith 5N aqueous sodium hydroxide solution (8 cc) and then with distilled water (25 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 6.5 cm, height 45 cm)
  7. washeluting with a mixture of dichloromethane and methanol (90:10) by volume) and
  8. customcollecting 120-cc fractions
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-ef52177e49b8495c8665014652f1b0bc
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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