Methanol → HCID 13657796, compound

HRID 1745850Notes

Reaction equation

HRID 1745850 reaction equation
[CH2:1]([C:8]1[CH2:12][C:11]([CH2:18][OH:19])([CH2:13]CC(O)=O)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+].C[OH:25]>>[CH2:1]([C:8]1[CH2:12][C:11]([CH2:13][OH:25])([CH2:18][OH:19])[O:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 22227101HCID 22227101, compound

Product 1

HCID 13657796HCID 13657796, compound

Conditions

Temperature
-10 °C

Procedure

In a 1 l flask, equipped with thermometer and mechanical stirrer, in a nitrogen atmosphere are added: 71.55 g (0.272 mol) of raw 3-benzyl-5-hydroxymethyl-5-carboxyethyl isoxazoline deriving from Example 3 and 553 ml of methanol. The solution is cooled to −10° C. and in the time period of 1 h are added: 10.29 g (0.272 mol) of NaBH4 granules (10–40 mesh). Once the addition is completed the temperature is increased up to room temperature and the solution is allowed to stir for 1 h 30′. Then are added 250 ml of a saturated ammonium chloride solution maintaining the temperature at approx. 20° C. The solvent is evaporated under vacuum (24 mbar at 25° C.). The residue is taken up with 150 ml of methylene chloride and the residue formed after evaporation is dissolved in a minimum quantity of water. The two phases obtained are separated and the aqueous one is retroextracted three times, each time with a volume of 100 ml, with methylene chloride. The organic phases are collected and dried with sodium sulphate. It is filtered and, after evaporation of the solvent, 59.85 g of a raw orange oil product are obtained. The raw product is crystallized in 150 ml of ethyl acetate and 140 ml of hexane. 39.91 g of 3-benzyl-5,5-bis(hydroxymethyl)isoxazoline as a pale yellow solid are obtained. Another 4.16 g of product are recovered from the mother liquors.

Workup

  1. customIn a 1 l flask, equipped with thermometer and mechanical stirrer, in a nitrogen atmosphere
  2. additionare added
  3. additionare added
  4. additionOnce the addition
  5. temperatureis increased up to room temperature
  6. temperaturemaintaining the temperature at approx. 20° C
  7. customThe solvent is evaporated under vacuum (24 mbar at 25° C.)
  8. customthe residue formed
  9. customafter evaporation
  10. dissolutionis dissolved in a minimum quantity of water
  11. customThe two phases obtained
  12. customare separated
  13. customThe organic phases are collected
  14. dry with materialdried with sodium sulphate
  15. filtrationIt is filtered
  16. customafter evaporation of the solvent, 59.85 g of a raw orange oil product
  17. customare obtained
  18. customThe raw product is crystallized in 150 ml of ethyl acetate

Sources & evidence

ORD record
ord-2eea7746fa7a4d73a12d0fd6eceb8632
Source dataset
uspto-grants-2006_03
Patent number
US07019154B2

Reaction notes

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