Triethylamine → HCID 66718156, compound

HRID 1514748Notes

Reaction equation

HRID 1514748 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13](O)=[O:14])=[C:11](/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:10][N:9]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].[OH-].[Na+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[C:11](/[CH:16]=[CH:17]/[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:10][N:9]=2)=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 66718186HCID 66718186, compound

Product 1

HCID 66718156HCID 66718156, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (E)-3-(5-fluoropyridin-2-yl)-5-styrylisoxazole-4-carboxylic acid (1.2 g, 3.7 mmol) and triethylamine (0.52 mL, 3.7 mmol) in THF (30 mL) was added dropwise at room temperature a solution of ethyl chloroformate (0.36 mL, 3.7 mmol) in THF (4 mL). After 1 h the triethylamine hydrochloride salt was filtered off and washed with a small amount of THF. The filtrate was added to a solution of sodium borohydride (354 mg, 9.4 mmol) in water (3.5 mL). After stirring for 1 h at 5° C. aqueous sodium hydroxide (1 M, 11 mL) was added. Extraction with ethyl acetate, drying over sodium sulfate, filtering and evaporation of the solvent followed by trituration with diisopropylether afforded the title compound (895 mg, 81%) as a white solid after purification by chromatography (SiO2, DCM). MS: m/e=297.2 [M+H]+.

Workup

  1. filtrationAfter 1 h the triethylamine hydrochloride salt was filtered off
  2. washwashed with a small amount of THF
  3. additionwas added
  4. extractionExtraction with ethyl acetate
  5. dry with materialdrying over sodium sulfate
  6. filtrationfiltering
  7. customevaporation of the solvent

Sources & evidence

ORD record
ord-21b5104ea49d4248b045045db14a1e6b
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

Loading…