Hydrochloric Acid → HCID 14985748, compound

HRID 1589044Notes

Reaction equation

HRID 1589044 reaction equation
[CH:1]([N:4]([CH:9]([CH3:11])[CH3:10])[C:5](=[O:8])[O:6][CH3:7])([CH3:3])[CH3:2].CN(CCN(C)C)C.[Li]CCCC.[C:25]1(=[O:29])[CH2:28][CH2:27][CH2:26]1.Cl>C1COCC1.CCOCC>[CH:9]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:8])[O:6][CH2:7][C:25]1([OH:29])[CH2:28][CH2:27][CH2:26]1)([CH3:11])[CH3:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 14496CyclobutanoneHCID 568417Carbamic acid, bis(1-methylethyl)-, methyl esterHCID 178418339Butyllithium

Product 1

HCID 14985748HCID 14985748, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

11.148 g (70 mmol) of methyl N,N-diisopropylcarbamate and 12.424 g (105 mmol) of TMEDA in 200 ml of THF are lithiated at -78° C. with 70 mmol of sec. BuLi. After 1 h, 2.453 g (35 mmol) of cyclobutanone are added in portions (about 500 mg every 30 min). The reaction is complete after 3 h (TLC checking) and the reaction mixture is treated in the cold with 100 ml of ether and 120 ml of 2N hydrochloric acid. After warming to room temperature, the phases are separated and the aqueous phase is extracted three times using 50 ml of ether each time. The combined organic phases are then freed from acid with 50 ml of saturated NaHCO3 solution and dried over magnesium sulphate. After the solvent has been stripped off in vacuo, a crude yield of 12.197 g is obtained, chromatographic purification of which on silica gel using ether/petroleum ether (1:1) gives 3.721 g (46.4% of theory) of the title compound as a colorless liquid.

Workup

  1. customare lithiated at -78° C. with 70 mmol of sec
  2. waitThe reaction is complete after 3 h
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted three times
  5. dry with materialdried over magnesium sulphate
  6. customa crude yield of 12.197 g is obtained
  7. customchromatographic purification of which on silica gel

Sources & evidence

ORD record
ord-d5348e6f40fe4d2fb7d29dc9c05add25
Source dataset
uspto-grants-1993_06
Patent number
US05223633

Reaction notes

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