Salicylaldehyde → Tert-butyl 3-(2-formylphenoxy)pyrrolidine-1-carboxylate

HRID 85115Notes

Reaction equation

HRID 85115 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:10]([N:17]1[CH2:21][CH2:20][CH:19](OS(C)(=O)=O)[CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][CH:20]1[CH2:19][CH2:18][N:17]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:21]1)=[O:5]

Participants

6

Reactant 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

Product 1

HCID 58278994Tert-butyl 3-(2-formylphenoxy)pyrrolidine-1-carboxylateYield 23.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Hydroxybenzaldehyde (25; 1.2 g, 9.8 mmol), N-Boc-3-(methylsulfonyloxy)pyrrolidine (29; 2.6 g, 9.8 mmol), K2CO3 (2.0 g, 14.7 mmol) and tetrabutyl ammonium iodide (300 mg, cat) in CH2Cl2 (20 mL) was stirred at 70-80° C. for 18 h. DMF was removed by concentration under reduced pressure. The resulting residue was diluted with EtOAc (100 mL), washed with water (50 mL), dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (pentane:EtOAc=1:10) to afford 676 mg of tert-butyl 3-(2-formylphenoxy)pyrrolidine-1-carboxylate 30 as an oil (yield: 23%).

Workup

  1. customDMF was removed by concentration under reduced pressure
  2. additionThe resulting residue was diluted with EtOAc (100 mL)
  3. washwashed with water (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography (pentane:EtOAc=1:10)

Sources & evidence

ORD record
ord-e8ac84473b154dedbd0a13d496ecee4e
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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