Sodium Iodide → HCID 57458742, compound

HRID 1673024Notes

Reaction equation

HRID 1673024 reaction equation
Cl[CH2:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4].[Na+].[I-:18].[O-][Mn](=O)(=O)=O.[K+]>CC(C)=O>[I:18][CH2:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 516875Potassium PermanganateHCID 4072501Tert-butyl 2-(2-chloroacetyl)pyrrolidine-1-carboxylate

Product 1

HCID 57458742HCID 57458742, compoundYield 116.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of tert-butyl 2-(2-chloroacetyl)pyrrolidine-1-carboxylate (5 g, 20.24 mmol) in 200 mL of acetone was added 3 g (20.24 mmol) of NaI. The reaction was let to stir at room temperature for 18 h. The reaction was monitored by TLC (20% EtOAc/hexanes, the plate was developed by KMnO4 stain). The reaction mixture was filtered over celite, concentrated and dried to afford tert-butyl 2-(2-iodoacetyl)pyrrolidine-1-carboxylate (8 g, 99% yield). 1H NMR (CDCl3): δ 1.45 (d, 9H), 1.99 (s, 3H), 2.20 (m, 1H), 3.50 (m, 2H), 4.90 (m, 2H), 4.50 (m, 1H).

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. concentrationconcentrated
  3. customdried

Sources & evidence

ORD record
ord-69023de958f5466ab144011265d6b3c1
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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