Isobutylene oxide → Ammonium Hydroxide

HRID 398383Notes

Reaction equation

HRID 398383 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:14](=[O:25])[CH:13]=3)[CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:26][C:27]1([O:30][CH2:29]1)[CH3:28]>CCO>[NH4+:9].[OH-:21].[OH:30][C:27]([CH3:29])([CH3:28])[CH2:26][N:9]1[CH2:10][C@H:11]([C:12]2[CH:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:14](=[O:25])[CH:13]=2)[C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8]1

Participants

5

Reactant 2

HCID 11208Isobutylene oxideHCID 70023968HCID 70023968, compound

Product 2

HCID 14923Ammonium HydroxideHCID 70023962HCID 70023962, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(cis-3-phenylpyrrolidin-4-yl)-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone from step 6 above (0.2 g, 0.54 mmol) and isobutylene oxide (1 mL) in EtOH (4 mL) was heated to reflux for 1 h. The solvent was removed in vacuo and the residue was purified by flash column chromatography using 96:4:0.2 CH2Cl2:MeOH:NH4OH as eluant to give the title compound as an oil (0.17 g; TLC Rf=0.3, 96:4:0.2 CH2Cl2:MeOH:NH4OH; HPLC RT=5.08 min, method A).

Workup

  1. temperatureto reflux for 1 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-e981e7f6d749424c9ea443d6c75400e2
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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