Potassium Hydroxide → 2-(tert-butoxycarbonylamino)ethoxy-N-methylamine
Reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][O:10][N:11](C)[C:12](OC)=O)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>>[C:1]([O:5][C:6]([NH:7][CH2:8][CH2:9][O:10][NH:11][CH3:12])=[O:17])([CH3:4])([CH3:3])[CH3:2]Participants
3
Conditions
- Temperature
- 90 °C
Procedure
A mixture of [2-(N-Methyl-N-methoxycarbonyl-aminooxy)-ethyl]-carbamic acid tert-butyl ester (630 mg, 2.54 mmol), as prepared in the previous step, KOH (439 mg, 6.65 mmol, 15% water), D2O (2.0 mL) was stirred at 90° C. for 18 h. The mixture was allowed to cool to room temperature (a bilayer formed), and extracted with DCM (2×10 mL). The organic layers were combined, dried (2×Na2SO4), and concentrated to give 408 mg of the title compound (contaminated with 10 mol % starting material) as a nearly colorless oil (2.15 mmol, 85% yield). 1H NMR (300 Hz, CDCl3) δ 3.72 (t, J=4.9 Hz, 2H), 3.33 (br t, J=4.7 Hz, 2H), 2.70 (s, 3H), 1.45 (s, 9H).
Workup
- temperatureto cool to room temperature (a bilayer
- customformed), and
- extractionextracted with DCM (2×10 mL)
- dry with materialdried (2×Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d01e6edda5a34f58abb94d3c4ad1990d
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07550474B2
Reaction notes
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