water acetonitrile CCl4 → 2-(Tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

To a solution of (3R)-tert-butyl 3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate (D32) (440 mg, 2.06 mmol) in a mixture MeCN/CCl4/H2O (6/6/9 ml), sodium periodate (1.76 g, 8.25 mmol) was added and the reaction stirred vigorously for 5 min before addition of Ruthenium trichloride (12.8 mg, 0.062 mmol). The resulting solution was stirred 18 hrs at RT then quenched by addition of isopropanol (6 ml). The resulting black mixture was diluted with Et2O (50 ml) and filtered through a celite pad. The filtrate was evaporated and the residue was dissolved in water, the pH was adjusted to pH˜9-10 with K2CO3 and the aqueous was washed with Et2O (3×30 ml). Aqueous was then acidified to pH˜4-5 and re-extracted with EtOAc (3×30 ml). Collected organics after solvent evaporation afforded the title compound (D33) (216 mg).

1. customthen quenched by addition of isopropanol (6 ml)
2. additionThe resulting black mixture was diluted with Et2O (50 ml)
3. filtrationfiltered through a celite pad
4. customThe filtrate was evaporated
5. dissolutionthe residue was dissolved in water
6. washthe aqueous was washed with Et2O (3×30 ml)
7. extractionre-extracted with EtOAc (3×30 ml)
8. customCollected organics after solvent evaporation

ORD record

ord-7a517cee9eb1492993b2cef8096136c8

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181279B2