Methylamine → Benzyl (2-(aminooxy)ethyl)carbamate

HRID 2228424Notes

Reaction equation

HRID 2228424 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][O:14][N:15]1C(=O)C2=CC=CC=C2C1=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.CN>C(O)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][O:14][NH2:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 13983475Benzyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

Product 1

HCID 13983481Benzyl (2-(aminooxy)ethyl)carbamateYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[2-(benzyloxycarbonylamino)ethoxy]phthalimide (1.36 g, 4.00 mmol), as prepared in the preceding step, in ethanol (20 mL) and tetrahydrofuran (20 mL) was added 40% methylamine (2.0 mL, 25 mmol) and the reaction was stirred at ambient temperature for 1 h. After evaporating the solvent, the residue was purified by flash column chromatography (75-100% ethyl acetate in hexanes) to give the title compound as a white solid (0.80 g, 95%). 1H-NMR (300 MHz, CDCl3) δ 7.36 (m, 5H), 5.47 (bs, 2H), 5.21 (bs, 1H), 5.10 (s, 2H), 3.72 (t, J=5.0 Hz, 2H), 3.44 (q, J=5.0 Hz, 2H).

Workup

  1. customAfter evaporating the solvent
  2. customthe residue was purified by flash column chromatography (75-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c4ab374dcdbc4feb8845b1cbf55013a4
Source dataset
uspto-grants-2002_07
Patent number
US06417161B1

Reaction notes

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