Butyl iodide → HCID 21906070, compound

HRID 1281999Notes

Reaction equation

HRID 1281999 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH2:16][CH2:17][CH2:18][CH3:19].[H-].[Na+]>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21906070HCID 21906070, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1 g (5 mmol) of 1-t-butoxycarbonyl-4-hydroxypiperidine and 2.8 g (15 mmol) of 1-iodobutane in 5 mL of DMP was added 330 mg (11 mmol) of NaH (80% dispersion in mineral oil) and the mixture was heated to 40° C. After 5 h, 20 mL of H2O was added to the reaction mixture and it was extracted with ethyl acetate. 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 1-t-butoxycarbonyl-4-(butoxy)piperidine. Removal of the BOC protecting group was achieved as described in Example 4, Step 2 to give the title compound.

Workup

  1. extractionwas extracted with ethyl acetate
  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=4:1)

Sources & evidence

ORD record
ord-91bf956a8f834ae0980dddea69916d9b
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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