Water → [1-Benzyl-3-(hydroxymethyl)azetidin-3-YL]methanol

HRID 978706

Reaction equation

HRID 978706 reaction equation
Br[CH2:2][C:3]1([CH2:11]Br)[CH2:8][O:7]C(C)(C)[O:5][CH2:4]1.C(=O)(O)[O-].[Na+].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CS(C)=O>[OH:7][CH2:8][C:3]1([CH2:4][OH:5])[CH2:2][N:25]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 145372285,5-Bis(bromomethyl)-2,2-dimethyl-1,3-dioxane

Product 1

HCID 20164320[1-Benzyl-3-(hydroxymethyl)azetidin-3-YL]methanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
135 °C

Procedure

A mixture of 30.2 g of 5,5-bis(bromomethyl)-2,2-dimethyl-1,3-dioxane (0.1 mol), 24.0 g of sodium bicarbonate and 50 ml of dimethyl sulfoxide was heated to 135° C. A solution of 10.7 g of benzylamine in 50 ml of DMSO was then added dropwise with stirring over 1.5 hours. After addition was complete, the mixture was stirred for 2.5 hours at 135° C. After cooling, 100 ml of DMSO and 20 ml of water were added and the solution was extracted with pentane. The extract was washed with water and then shaken with 5% (w/w) sulfuric acid in order to extract the basic 3,3-bis(hydroxymethyl)-1-benzylazetidine acetone acetal.

Workup

  1. additionAfter addition
  2. stirringthe mixture was stirred for 2.5 hours at 135° C
  3. temperatureAfter cooling
  4. extractionthe solution was extracted with pentane
  5. washThe extract was washed with water
  6. stirringshaken with 5% (w/w) sulfuric acid in order
  7. extractionto extract the basic 3,3-bis(hydroxymethyl)-1-benzylazetidine acetone acetal

Sources & evidence

ORD record
ord-42a29bca230b451e8b083a3c67f98fe8
Source dataset
uspto-grants-1987_05
Patent number
US04665197

Linked notes

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