Diethyl Ether → Carbamic acid, (6-methyl-4-oxoheptyl)-, 1,1-dimethylethyl ester

HRID 352113Notes

Reaction equation

HRID 352113 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH2:14]([Mg]Br)[CH:15]([CH3:17])[CH3:16].C(OCC)C>O1CCCC1>[CH3:11][C:10]([O:9][C:7](=[O:8])[NH:3][CH2:4][CH2:5][CH2:6][C:2](=[O:1])[CH2:14][CH:15]([CH3:17])[CH3:16])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 3790001-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl esterHCID 178418816HCID 178418816, compound

Product 1

HCID 88013382Carbamic acid, (6-methyl-4-oxoheptyl)-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,1-dimethylethyl 2-oxo-1-pyrrolidinecarboxylate (7.5 g, 40.5 mmol) in dry tetrahydrofuran (150 ml) under a nitrogen atmosphere and at −78° C., was treated dropwise with a solution of isobutyl magnesium bromide in diethyl ether (2 molar, 22.5 ml, 45 mmol). The mixture was stirred at −78° C. for 2h then quenched into a saturated aqueous solution of ammonium chloride (100 ml). The products were extracted into ethyl acetate (2×250 ml) and the combined extracts dried over magnesium sulphate. Concentration of the extracts gave an oil which was purified on silica gel using isohexane/diethylether (1:1). The title compound was isolated as a colourless oil (2.3 g, 25%).

Workup

  1. customthen quenched into a saturated aqueous solution of ammonium chloride (100 ml)
  2. extractionThe products were extracted into ethyl acetate (2×250 ml)
  3. dry with materialthe combined extracts dried over magnesium sulphate
  4. customConcentration of the extracts gave an oil which
  5. customwas purified on silica gel

Sources & evidence

ORD record
ord-97f9ab441dd840058d6d95d7def96351
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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