Triethylamine → Tert-butyl 6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate

To a solution of (3-Aza-bicyclo[3.1.0]hex-6-yl)-methanol-HCl (11.8 gm, 78.7 mmol) in 350 mL of anhydrous CH2Cl2 at room temperature was added Et3N (32.9 mL, 236 mmol), followed by (BOC)2O (18.9 gm, 86.6 mmol) in portions. The reaction was stirred at room temperature for 18 hours. The mixture was washed with saturated NaHCO3, water, brine and dried over anhydrous MgSO4. The mixture was filtered and concentrated under reduced pressure to yield the crude material, which was purified via flash chromatography with 10% MeOH/EtOAc. The product containing fractions were collected and concentrated to yield the desired product (15.6 gm). 400 MHz 1H NMR (CDCl3) δ 3.42-3.56 (m, 4H), 3.24-3.37 (m, 2H), 1.72 (brs, 1H), 1.37-1.41 (m, 10H), 0.87-0.93 (m, 1H); MS (M+1) 213.2.

1. washThe mixture was washed with saturated NaHCO3, water, brine
2. dry with materialdried over anhydrous MgSO4
3. filtrationThe mixture was filtered
4. concentrationconcentrated under reduced pressure
5. customto yield the crude material, which
6. customwas purified via flash chromatography with 10% MeOH/EtOAc
7. additionThe product containing fractions
8. customwere collected
9. concentrationconcentrated

ORD record

ord-8305a108d4c54e7e806300195f1af794

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473787B2