Water → 4-(Methoxymethyl)piperidine
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=O)(C)(C)C.I[CH3:17].[H-].[Na+].O>CN(C=O)C>[CH3:17][O:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 0.1 g (0.46 mmol) of 1-t-butoxycarbonyl-4-hydroxymethylpiperidine and 0.1 mL (1.6 mmol) of iodomethane in 2.5 mL of DMF was added 0.022 g (0.92 mmol) of NaH (80% dispersion in mineral oil). After 2 h, 10 mL of H2O was added to the reaction mixture and it was extracted with ether. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate=4:1) to give the title compound.
Workup
- extractionwas extracted with ether
- washThe combined organic fractions were washed with sat'd NaCl solution
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customThe residue was purified by chromatography (silica, hexanes:ethyl acetate=4:1)
Sources & evidence
- ORD record
- ord-dd9a48cb5ccc45a083443b7d4d19caec
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455548B2
Reaction notes
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