Methyl iodide → Methyl N-Boc-4-piperidinepropionate

HRID 643568Notes

Reaction equation

HRID 643568 reaction equation
IC.[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:21]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOCC>[CH3:21][O:19][C:18](=[O:20])[CH2:17][CH2:16][CH:13]1[CH2:14][CH2:15][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[CH2:11][CH2:12]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acid

Product 1

HCID 1502093Methyl N-Boc-4-piperidinepropionate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Iodomethane (556 μL, 8.93 mmol) was added dropwise to a cooled (0° C.) mixture of commercially available 3-[1-(tert-butoxycarbonyl)piperidin-4-yl]propanoic acid (2.09 g, 8.12 mmol) and K2CO3 (2.81 g, 20.3 mmol) in 20 mL of DMF. The reaction mixture was permitted to warm to rt and stir overnight. The reaction mixture was diluted with ether and washed four times with water, then once with brine. The ethereal layer was dried over anhydrous MgSO4, filtered, and concentrated. Purification by MPLC (silica, 40% ethyl acetate/hexanes) provided tert-butyl 4-(3-methoxy-3-oxopropyl)piperidine-1-carboxylate.

Workup

  1. temperaturea cooled
  2. washwashed four times with water
  3. dry with materialThe ethereal layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by MPLC (silica, 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dfad64d184d14deab47853859e97bfa8
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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