Ammonium Chloride → HCID 23366071, compound

To a suspension of NaBH4 (14.35 g, 379.3 mmol) in EtOH (200 mL) was added dropwise a solution of 23 (11.2 g, 37.93 mmol) in EtOH (100 mL) and the mixture was refluxed for 16 hours. After addition of an aqueous NH4Cl solution (5%, 150 mL) in small portions, the solution was distilled under vacuum to remove EtOH. CH2Cl2 (200 mL) was added and the mixture was filtered. The two layers were separated, and the aqueous phase was extracted with CH2Cl2 (3×50 mL). The combined organic phases were washed with aqueous NaHCO3 (5%, 100 mL), dried over MgSO4 and concentrated under vacuum. The resulting yellow oil was recrystallized from EtOAC/hexane to give off-white powder 24 (6.81 g, 85% yield).

1. temperaturethe mixture was refluxed for 16 hours
2. distillationthe solution was distilled under vacuum
3. customto remove EtOH
4. additionCH2Cl2 (200 mL) was added
5. filtrationthe mixture was filtered
6. customThe two layers were separated
7. extractionthe aqueous phase was extracted with CH2Cl2 (3×50 mL)
8. washThe combined organic phases were washed with aqueous NaHCO3 (5%, 100 mL)
9. dry with materialdried over MgSO4
10. concentrationconcentrated under vacuum
11. customThe resulting yellow oil was recrystallized from EtOAC/hexane

ORD record

ord-e3318320f7fe4fa2b87deadb361bf6de

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353120B2