Phosphoric Acid → HCID 53695575, compound

HRID 1596041Notes

Reaction equation

HRID 1596041 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]=[CH:13][C:14](O)=[O:15].C(N(CC)CC)C.ClC(OC)=O.[BH4-].[Na+].OP(O)(O)=O>C1COCC1.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]=[CH:13][CH2:14][OH:15]

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 53401548HCID 53401548, compound

Product 1

HCID 53695575HCID 53695575, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 3B (4.66 g, 16.9 mmol) and triethylamine (2.70 mL, 19.4 mmol) in THF (25 mL) at −20° C. was added methyl chloroformate (1.60 mL, 10.3 mmol), and the resulting solution was stirred for 15 minutes. This solution was then added to sodium borohydride (1.92 g, 50.6 mmol) in water (10 mL) at 0° C., stirred at room temperature for 2 hours, acidified with 0.5 M H3PO4, and extracted with ethyl acetate. The ethyl acetate was washed with water, brine, dried (MgSO4), filtered, and concentrated to provide 2.10 g (47%) of the desired compound.

Workup

  1. stirringstirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d096e638fae44d359c2ff4d63c54cee2
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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