Water → HCID 86738630, compound

HRID 2198780Notes

Reaction equation

HRID 2198780 reaction equation
[CH:1]12[O:7][CH:6]1[CH2:5][CH2:4][CH2:3][C:2]2=[O:8].[CH2:9]=[CH2:10].[CH3:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH2:20]>>[OH:7][C@H:1]1[C@H:6]([N:12]([CH3:11])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3][C:2]21[O:8][CH2:10][CH2:9][O:20]2

Participants

4

Reactant 3

HCID 962Water2×HCID 7669N-MethylbenzylamineHCID 20453212HCID 20453212, compound

Product 1

HCID 86738630HCID 86738630, compoundYield 100%

Procedure

A mixture of 40.6 g (0.26 mole) of spiro[1,3-dioxolane]-2,2'-[7-oxabicyclo[4.1.0]heptane], also named 7-oxabicyclo-[4.1.0]-heptan-2-one-ethylene ketal1, 32.7 g (0.25 mole) of methyl(phenylmethyl)amine and 35 ml of water was heated on a steambath with stirring for 1.5 hour. The reaction mixture was allowed to stir at ambient temperature overnight. The mixture was then treated with an additional 500 ml of water and steam distilled until the distillate was clear. The residue was distributed between methylene chloride and water. The liquid phases were separated and the aqueous phase was extracted with methylene chloride. The combined organic phases were dried over magnesium sulfate and concentrated in vacuo leaving 71.6 g (100% yield) of crude trans-(∓)-6-hydroxy-N-methyl-N-(phenylmethyl)-1,4-dioxaspiro[4.5]decan-7-amine intermediate.

Workup

  1. temperaturewas heated on a steambath
  2. stirringto stir at ambient temperature overnight
  3. distillationdistilled until the distillate
  4. customThe liquid phases were separated
  5. extractionthe aqueous phase was extracted with methylene chloride
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e5af0f5ddc84be3adeb895493c30481
Source dataset
uspto-grants-1982_11
Patent number
US04359476

Reaction notes

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