tert-Butanol → HCID 59190362, compound

To a stirred solution of (R)-4-allyl-1-((S)-1-(4-bromophenyl)ethyl)-4-phenyl-1,3-diazepan-2-one (51 mg, 0.12 mmol) in THF (2 mL) and water (2 mL) were added NaIO4 (132 mg, 0.62 mmol) and 2.5% OSO4 in t-BuOH (0.032 mL, 0.003 mmol). The mixture was stirred at rt for 5 h and concentrated under reduced pressure. The residue was partitioned between EtOAc (90 mL) and brine (20 mL). The organic layer was concentrated and the residue was dissolved in MeOH (20 mL). The solution was cooled in an ice bath and NaBH4 (50 mg) was added. The mixture was stirred overnight and concentrated. The residue was taken up in EtOAc (90 mL), washed with 5% aq HCl (20 mL) and satd aq NaHCO3 (20 mL), and dried over Na2SO4. Removal of the solvent left an oil (43 mg) which was purified by prep HPLC to afford (R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-hydroxyethyl)-4-phenyl-1,3-diazepan-2-one (19 mg, 37%) as an oil. LC-MS Method 2 tR=8.7 min, m/z=419, 417; 1H NMR (CDCl3) δ 1.0-1.2 (2H), 1.23 (d, 3H), 1.77 (m, 1H), 2.01 (m, 1H), 2.24 (m, 2H), 2.66 (m, 1H), 2.89 (m, 1H), 3.45 (m, 1H), 3.72 (m, 1H), 4.10 (br s, 1H), 5.50 (q, 1H), 6.79 (s, 1H), 7.24 (3H), 7.37 (2H), 7.43 (4H)

1. concentrationconcentrated under reduced pressure
2. customThe residue was partitioned between EtOAc (90 mL) and brine (20 mL)
3. concentrationThe organic layer was concentrated
4. dissolutionthe residue was dissolved in MeOH (20 mL)
5. temperatureThe solution was cooled in an ice bath
6. additionNaBH4 (50 mg) was added
7. stirringThe mixture was stirred overnight
8. concentrationconcentrated
9. washwashed with 5% aq HCl (20 mL)
10. dry with materialdried over Na2SO4
11. customRemoval of the solvent
12. waitleft an oil (43 mg) which
13. customwas purified by prep HPLC

ORD record

ord-97818b25c307479db48204d11182d5b7

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202857B2