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/CH2Cl2. The product containing fractions were collected and concentrated to yield 6-Hydroxymethyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (15.6 gm). 400 MHz 1H NMR (CDCl3) δ 3.4-3.6 (m, 4H), 3.2-3.7 (m, 2H), 1.72 (brs, 1H), 1.4-1.4 (m, 10H), 0.9-0.9 (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/CH2Cl2
7. additionThe product containing fractions
8. customwere collected
9. concentrationconcentrated

ORD record

ord-d4a1dc305ac4463ba119d6e364cd582e

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124639B2