Sodium Hydroxide → HCID 86762551, compound

Participants

Reaction Conditions

Reaction Steps

t-Boc-NH2 (MW 108.57, 9.8 g, 0.0837 mol, 2.95 eq) was dissolved in n-PrOH (110 mL) in a 1 L RB flask, The solution was treated with NaOH (MW 40, 3.6 g, 0.9 mol, 3.17 eq) in H2O (220 mL) and tert-Butyl hypochlorite (MW 108.57, 10 mL, 0.0868 mol, 3.06 eq). After stirring for 20 minutes, the solution was cooled to 0° C. A solution of (DHQ)2phal (MW 779, 0.43 g, 0.552 mmol, 0.019 eq) in n-PrOH (110 mL) was added. A solution of propyl 4-vinylbenzoate (MW 190.24, 5.41 g, 0.0284 mol, 1 eq) in n-PrOH (220 mL) was then added, followed by the addition of K2OsO4 (MW 368.43, 427 mg, 0.00116 mol, 0.04 eq). The reaction mixture was stirred at 0° C. and monitored by LC/MS and TLC. After stirring at 0° C. for 2 hours, the reaction was quenched with sat. Na2SO3 and n-PrOH was removed under vacuum. The residue was diluted with water and extracted with EtOAc (3×). The combined EtOAc fraction was washed with 5% HCl (1×) and brine (1×). After drying over Na2SO4 and filtration, the filtrate was concentrated under vacuum to dryness. The residue was purified on a silica gel column, eluted with EtOAc/Hexanes (10-40%) to give 5.17 g (56% yield) of the pure 1-3. The 1H NMR (DMSO-d6) data is depicted in FIG. 3.

Provenance & Evidence