Hydrochloric Acid → HCID 10934012, compound

Participants

Reaction Steps

(1S,2S,3R,4R)-3-tert-Butoxycarbonylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (R)-1-phenyl-ethylamine salt (10.0 g, 26.7 mmol) in Ethyl acetate (200 mL, 2000 mmol;) and Water (100 mL, 6000 mmol;) was added 1 M of Hydrogen Chloride in Water (50 mL) via pipette to pH 2. The layers were separated and the aqueous was extracted (EtOAc), drying of combined organics (MgSO4) provided (1S,2S,3R,4R)-3-tert-Butoxycarbonylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid as a white foamy solid 6.74 grams 1H-NMR (CDCL3, 400 MHz): δ 12.30 (broad peak 1H) m 6.99 (d, J=9.6 Hz, 1H), 6.20 (vroad s, 2H), 3.97 (t, J=9.6 Hz, 1H), 3.05 (s, 1H), 2.74 (s, 1H), 2.60 (d, J=8.4 Hz, 1H), 2.09 (d, J=9.6 Hz, 1H), 1.66 (d, J=9.6 Hz, 1H), 1.46 (s, 9H).

Provenance & Evidence