Sodium Hydroxide → 3-Cyclohexyl-3-methylaminomethyloxetane

HRID 704156Notes

Reaction equation

HRID 704156 reaction equation
[CH:1]1([C:7]2([CH:11]=O)[CH2:10][O:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].Cl.CN.[C:21]([BH3-])#[N:22].[Na+].[OH-].[Na+]>CO>[CH:1]1([C:7]2([CH2:11][NH:22][CH3:21])[CH2:10][O:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 200755923-Cyclohexyl-3-formyloxetane

Product 1

HCID 200755603-Cyclohexyl-3-methylaminomethyloxetane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-Cyclohexyl-3-formyloxetane (1.7 g) was dissolved in methanol (10 ml) at 25° C. In succession, anhydrous sodium acetate (3.3 g), methylamine hydrochloride (3.4 g) and sodium cyanoborohydride (630 mg) were added, followed by a further volume of methanol (30 ml). The mixture was stirred overnight and then basified with sodium hydroxide solution (1M, 22 ml) to pH9. Ether extraction, washing and drying, followed by evaporation gave 3-cyclohexyl-3-methylaminomethyloxetane as a colourless oil.

Workup

  1. extractionEther extraction
  2. washwashing
  3. customdrying
  4. customfollowed by evaporation

Sources & evidence

ORD record
ord-4ab2bc696400457f85850ebfb5c9d34d
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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