Hydrazine hydrate (1:1) → HCID 20737794, compound

HRID 350484Notes

Reaction equation

HRID 350484 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]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69332185HCID 69332185, compound

Product 1

HCID 20737794HCID 20737794, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 7.5 h
  3. filtrationThe solution was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionThe residue was poured into aq
  6. extractionNaHCO3 and extracted with CHCl3
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5dbe499dda27409d897c98061dc81411
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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