Sodium borohydride → Carbamic acid 3-[4-(2-hydroxy-ethoxy)-phenyl]-isoxazol-5-ylmethyl ester

HRID 72318Notes

Reaction equation

HRID 72318 reaction equation
[BH4-].[Na+].C([O:5][C:6](=O)[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[O:17][N:16]=2)=[CH:11][CH:10]=1)C>C1COCC1>[OH:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[O:17][N:16]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66617666HCID 66617666, compound

Product 1

HCID 46892997Carbamic acid 3-[4-(2-hydroxy-ethoxy)-phenyl]-isoxazol-5-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 equivalents of NaBH4 was added to 200 mg of the compound [4-(5-carbamoyloxymethyl-isoxazol-3-yl)-phenoxy]-acetic acid ethyl ester in Example 47 while stirring in the presence of a 10 ml THF/5 ml water solvent. After stirring for 12 hours, the solvent was distilled off under reduced pressure and 20 ml of 1-N HCl solution was added to the reactants, followed by extraction three times with 20 ml of ethyl acetate. The obtained organic layer was put under reduced pressure to obtain carbamic acid 3-[4-(2-hydroxy-ethoxy)-phenyl]-isoxazol-5-ylmethyl ester as a desired compound.

Workup

  1. distillationthe solvent was distilled off under reduced pressure and 20 ml of 1-N HCl solution
  2. additionwas added to the reactants
  3. extractionfollowed by extraction three times with 20 ml of ethyl acetate

Sources & evidence

ORD record
ord-2260209b56684bc0859a3ead21aba189
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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