Hydrazine hydrate (1:1) → HCID 20737794, compound
Reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([N:15]1C(=O)C2=CC=CC=C2C1=O)[CH2:11][CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CCO>[NH2:15][C@@H:10]([CH2:11][CH2:12][CH:13]=[CH2:14])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1-benzyloxy-2-(S)-phthalimido-5-hexene (2.95 g, 8.80 mmol) in EtOH (30 ml) was added hydrazine hydrate (80% in water, 460 ml, 11.4 mmol) at rt, and the resulting mixture was heated under reflux for 7.5 h with stirring. The solution was filtered, and the filtrate was concentrated in vacuo. The residue was poured into aq.NaHCO3 and extracted with CHCl3. The organic layer was dried over anhydrous Na2SO4, then concentrated in vacuo to give 2-(S)-amino-1benzyloxy-5-hexene (1.90 mg, quant.) as a colorless oil. 1H-NMR (CDCl3) δ 1.37–1.55 (series of m, 4 H), 2.08–2.19 (m, 2 H), 2.99–3.03 (m, 1 H), 3.25 (dd, J=9.2, 7.6 Hz, 1 H), 3.45 (dd, J=9.2, 4.0 Hz, 1 H), 4.53 (s, 2 H), 4.94–5.06 (series of m, 2 H), 5.76–5.85 (m, 1 H), 7.27–7.37 (m, 5 H); MS (ESI) m/z, 206 (M++H), 247 (M++H+CH3CN).