Methylhydrazine → HCID 14814232, compound

HRID 1089264Notes

Reaction equation

HRID 1089264 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([O:21][N:22]1C(=O)C2=CC=CC=C2C1=O)[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CNN>ClCCl>[CH2:1]([O:8][CH2:9][C@H:10]([O:21][NH2:22])[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6061Methylhydrazine2×HCID 14814230HCID 14814230, compound

Product 1

HCID 14814232HCID 14814232, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-N-(1,4-dibenzyloxybut-2-oxy)phthalimide (0.6 g, 1.3 mmol) in dichloromethane (5 ml) was treated with methylhydrazine (86 μl, 1.6 mmol). A deep red colouration developed, disappearing gradually as a white solid precipitated out of solution. After stirring at room temperature for 30 minutes additional methylhydrazine (8 μl, 0.15 mmol) was added. The mixture was stirred at room temperature for an additional 30 minutes, filtered and the filtrate washed with 3% sodium carbonate solution (5 ml). The organic phase was dried (MgSO4), the solvent removed under reduced pressure and the residue chromatographed on silica eluting with ethyl acetate-hexane to give (R)-1,4-dibenzyloxybut-2-oxyamine (0.32 g, 77%), [α]D25 +10.1° (c 0.14 in ethanol); IR: υmax (film) 3310, 3250, 3090, 3060, 3030, 2920, 2860, 1585, 1495, 1450, 1365, 1310, 1200, 1100, 1030, 950, 915, 740, 700 cm-1 ; 1H NMR: δH (CDCl3) 1.85 (2H, m, CH2), 3.55 (4H, m, 2×CH2), 3.90 (1H, m, CH), 4.49 (2H, s, CH2), 4.45 (2H, s, CH2), 5.36 (2H, s, D2O exchangeable NH2) 7.35 (10H, m, 2×C6H5); m/z 302 (MH+), 301 (M+, 3%), 181 (5), 163 (10), 106 (15), 105 (5), 92 (15), 91 (100), 71 (15), 65 (10). M+ observed 301.1670; C18H23NO3 requires M+ 301.1678.

Workup

  1. customprecipitated out of solution
  2. additionwas added
  3. filtrationfiltered
  4. washthe filtrate washed with 3% sodium carbonate solution (5 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customthe residue chromatographed on silica eluting with ethyl acetate-hexane

Sources & evidence

ORD record
ord-13701896b73a4c159696e1f977f734b0
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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