Sodium Iodide → Iodomethyl n-tert-butoxycarbonyl-4-piperidylcarboxylate

HRID 588043Notes

Reaction equation

HRID 588043 reaction equation
[Na+].[I-:2].[N:3]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH2:12]Cl)=[O:10])[CH2:5][CH2:4]1>C(#N)C>[N:3]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH2:12][I:2])=[O:10])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 101075661-Tert-butyl 4-chloromethyl piperidine-1,4-dicarboxylate

Product 1

HCID 59443277Iodomethyl n-tert-butoxycarbonyl-4-piperidylcarboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of NaI (1.6 g, 11.09 mmol) in dry acetonitrile (8 mL) was added dropwise 1-tert-butyl 4-chloromethyl piperidine-1,4-dicarboxylate (2.8 g, 10.08 mmol) in 2 mL of acetonitrile. The mixture turned dark orange and was stirred at rt in the dark for 24 h. The reaction mixture was filtered to remove NaCl and the filtrate was concentrated in vacuo. The remaining residue was partitioned between DCM and 5% aq NaHSO3 solution. The organic layer was washed with water and brine, dried (Na2SO4), and concentrated in vacuo to give 1-tert-butyl 4-iodomethyl piperidine-1,4-dicarboxylate as a pale yellow oil (3.5 g, 94%). Attempts to characterize by NMR in DMSO-d6 resulted in rapid decomposition. The material was stored in the dark at −20° C. to minimize decomposition before further use. LCMS: MH=370.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove NaCl
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe remaining residue was partitioned between DCM and 5% aq NaHSO3 solution
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3650df2cfb2b4d27a82f26ba02436066
Source dataset
uspto-grants-2016_01
Patent number
US09227954B2

Reaction notes

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