Sodium Iodide → HCID 131731894, compound

HRID 81114Notes

Reaction equation

HRID 81114 reaction equation
[CH2:1]([N:8]([C:23](=[O:26])[CH2:24]Cl)[C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C@H:10]1[OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-:28]>CC#N>[CH2:1]([N:8]([C:23](=[O:26])[CH2:24][I:28])[C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C@H:10]1[OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 131731895HCID 131731895, compound

Product 1

HCID 131731894HCID 131731894, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of trans-tert-butyl 4-[benzyl(chloroacetyl)amino]-3-hydroxypiperidine-1-carboxylate (144 g, 376 mmol) in CH3CN (2 L) was added NaI (56.4 g, 376 mmol) in one portion. The mixture was stirred at reflux for 1 h and then concentrated. The residue was dissolved in DCM (1 L) and filtered. The filtrate was concentrated under reduced pressure to afford trans-tert-butyl 4-[benzyl(iodoacetyl)amino]-3-hydroxypiperidine-1-carboxylate, which was used directly in the next step without further purification.

Workup

  1. temperatureat reflux for 1 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DCM (1 L)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c2783cae4986471a86b78c8d8af456e8
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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