Triethylamine → HCID 23159221, compound

To a solution of 5-phenylisoxazole-3-carbaldehyde (500 mg, 2.89 mmol) in MeOH (10 mL) at 0° C., was added NaBH4 (327 mg, 8.67 mmol). The reaction was slowly warmed to room temperature, stirred for 15 h and concentrated in vacuo. The solid obtained was dissolved in EtOAc, washed with H2O (1×) and saturated NH4Cl (3×). The organic layers were combined, dried over MgSO4, filtered, concentrated and dissolved in anhydrous CH2Cl2 (8 mL). The mixture was cooled to 0° C., followed by addition of Et3N (1.02 mL, 7.25 mmol) and methanesulfonyl chloride (337 μL, 4.35 mmol). The reaction was slowly warmed to room temperature and stirred for 15 h. Upon completion, the reaction was quenched with aqueous NaHCO3 (5 mL) and extracted with EtOAc. The combined organic layers were washed with NaHCO3 (2×), dried over MgSO4, filtered, concentrated and carried onto the next step without further purification.

1. concentrationconcentrated in vacuo
2. customThe solid obtained
3. washwashed with H2O (1×) and saturated NH4Cl (3×)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutiondissolved in anhydrous CH2Cl2 (8 mL)
8. temperatureThe mixture was cooled to 0° C.
9. temperatureThe reaction was slowly warmed to room temperature
10. stirringstirred for 15 h
11. customUpon completion, the reaction was quenched with aqueous NaHCO3 (5 mL)
12. extractionextracted with EtOAc
13. washThe combined organic layers were washed with NaHCO3 (2×)
14. dry with materialdried over MgSO4
15. filtrationfiltered
16. concentrationconcentrated
17. customcarried onto the next step without further purification

ORD record

ord-25341196c12444f48f06c5060268b335

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842324B2