Water → HCID 70006334, compound

To a solution of (62) (5 g) in Benzene (50 mL) p-TSA (500 mg) was added and the resulting mixture was heated at reflux for 6 hr. while water formed in the reaction was removed using a Dean-Stark Trap. The reaction mixture was allowed to cool down to room temperature and washed with water (5×50 mL). The organic layer was concentrated in vacuo to obtain an oil which was dried on a high vacuum and directly used in next step. To a solution of above product (4.8 g) in 1:1 t-BuOH/H2O (100 mL) was treated with NMO (3 g) and OsO4 (380 mg). The resulting mixture was stirred at RT for 12 hr. Aq. NaHCO3 (300 mL) and EtOAc (300 mL) were then added, and the product was extracted in to EtOAc. Organic phase was separated, and the concentrated in vacuo to obtain compounds (80) and (84) which were separated on silica (EtOAc:Hexane 2:3).

1. temperaturethe resulting mixture was heated
2. temperatureat reflux for 6 hr
3. customwas removed
4. washwashed with water (5×50 mL)
5. concentrationThe organic layer was concentrated in vacuo
6. customto obtain an oil which
7. customwas dried on a high vacuum
8. additionTo a solution of above product (4.8 g) in 1:1 t-BuOH/H2O (100 mL) was treated with NMO (3 g) and OsO4 (380 mg)
9. additionAq. NaHCO3 (300 mL) and EtOAc (300 mL) were then added
10. extractionthe product was extracted in to EtOAc
11. customOrganic phase was separated
12. concentrationthe concentrated in vacuo

ORD record

ord-36117cb519364ee48ea67e15ce0dcebd

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06545033B1