Water → 4-(3-Hydroxypropyloxymethyl)piperidine

HRID 1282003Notes

Reaction equation

HRID 1282003 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.Br[CH2:17][CH2:18][CH2:19][O:20][Si](C(C)C)(C(C)C)C(C)C.[H-].[Na+].O>CN(C=O)C>[OH:20][CH2:19][CH2:18][CH2:17][O:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 23510097(3-Bromopropoxy)tri(propan-2-yl)silane

Product 1

HCID 184234304-(3-Hydroxypropyloxymethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.5 g (2.3 mmol) of 1-t-butoxycarbonyl-4-hydroxymethylpiperidine and 1.4 g (4.6 mmol) of 1-bromo-3-(triisopropylsilyloxy)propane in 3 mL of DMF was added 0.12 g (4.1 mmol) of NaH (60% dispersion in mineral oil) and the reaction mixture was stirred at rt for 16 h. To the reaction mixture was added 10 mL of H2O 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=19:1) to give the title compound.

Workup

  1. extractionwas extracted with ether
  2. washThe combined organic fractions were washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-f4db2b8ac2b04ccd97831f461433e027
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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