Potassium Iodide → HCID 18391976, compound

HRID 618184Notes

Reaction equation

HRID 618184 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][NH:11][CH:10]1[C:22]#[N:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CC(C)=O>[CH2:32]([N:11]1[CH2:12][C@@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]1[C:22]#[N:23])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18391977HCID 18391977, compound

Product 1

HCID 18391976HCID 18391976, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (3R,4R)-3,4-dibenzyloxy-pyrrolidine-2-carbonitrile (13 g, 42.2 mmol), potassium carbonate (8.7 g, 63 mmol), potassium iodide (0.1 g), benzyl bromide (7.5 ml, 63.2 mmol) and acetone (200 ml) were heated at reflux temperature for 4 hours. The mixture was cooled, filtered and the filtrate evaporated to dryness in vacuo to give the title compound as an oil. Purification of the crude product on a silica gel column (Eluent: From 100% heptane to 100% ethyl acetate) afforded (3R,4R)-1-benzyl-3,4-dibenzyloxy-pyrrolidine-2-carbonitrile (8.2 g, yield: 49%) as an oil.

Workup

  1. temperaturewere heated
  2. temperatureat reflux temperature for 4 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-87685250a040420cabc6f1279c3e5fd7
Source dataset
uspto-grants-1999_09
Patent number
US05952363

Reaction notes

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