Reaction #1747901

Reaction equation

7-tert-butoxycarbonyl-2-{4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2-methoxy-5-pyridinyl}-7-azabicyclo[2.2.1]hept-2-ene

tetrabutylammonium fluoride

water

EtOAc

→

7-tert-butoxycarbonyl-2-[4-(2-hydroxyethyl)-2-methoxy-5-pyridinyl]-7-azabicyclo[2.2.1]hept-2-ene

Yield 100.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   OtherThe organic layer was separated
2. 2
   Washwashed with brine
3. 3
   Dryingdried (Na2SO4)
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was purified by chromatography with hexane/EtOAc (2:1)

Procedure

To a stirred solution of 7-tert-butoxycarbonyl-2-{4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2-methoxy-5-pyridinyl}-7-azabicyclo[2.2.1]hept-2-ene (360 mg, 0.78 mmol) in anhydrous THF (8 mL) was added 1.56 mL (1.56 mmol) of 1 M tetrabutylammonium fluoride in THF. The reaction solution was stirred at room temperature for 6 h, and then poured into a mixture of water (10 mL) and EtOAc (60 mL). The organic layer was separated and washed with brine, dried (Na2SO4), and concentrated. The residue was purified by chromatography with hexane/EtOAc (2:1) to afford 7-tert-butoxycarbonyl-2-[4-(2-hydroxyethyl)-2-methoxy-5-pyridinyl]-7-azabicyclo[2.2.1]hept-2-ene as a syrup (270 mg, 100%). 1H NMR (CDCl3) δ 7.82 (s, 1H), 6.66 (s, 1H), 6.20 (s, 1H), 4.91 (s, 1H), 4.78 (s, 1H), 3.91 (s, 3H), 3.77 (br s, 2H), 3.20-2.85 (m, 2H), 2.40 (br s, 1H), 2.10-1.89 (m, 2H), 1.44 (s, 9H), 1.36-1.16 (m, 2H); 13C NMR (CDCl3) δ 164.05, 156.36, 149.36, 145.98, 144.61, 132.12, 123.75, 111.27, 80.38, 62.92, 62.28, 61.45, 53.33, 36.88, 28.16, 25.83, 23.46. MS m/z (%): 346 (M+, 1), 318 (8), 262 (100), 218 (12), 199 (21). Anal. Calcd for (C19H26N2O4. 1/3H2O) C, 64.75; H, 7.63; N, 7.95. Found: C, 64.55; H, 7.29; N, 7.64.

Source