Hydrochloric Acid → HCID 14985749, compound

HRID 1589045Notes

Reaction equation

HRID 1589045 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]C(CC)C.[CH:25](=[O:29])[CH:26]([CH3:28])[CH3:27].Cl>C1COCC1.CCOCC>[CH:9]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:8])[O:6][CH2:7][CH:25]([OH:29])[CH:26]([CH3:28])[CH3:27])([CH3:11])[CH3:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6561IsobutyraldehydeHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 568417Carbamic acid, bis(1-methylethyl)-, methyl esterHCID 178418400CID 53628100

Product 1

HCID 14985749HCID 14985749, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

478 mg (3 mmol) of methyl N,N-diisopropylcarbamate are lithiated with 392 mg (3.3 mmol) of TMEDA in 4 ml of THF at -78° C. using 3.3 mmol of sec-BuLi. After 1 h, the reaction mixture is treated with 144 mg (2 mmol) of isobutyraldehyde and stirred for 21 h. The reaction mixture is then treated at -78° C. with 10 ml of 2N hydrochloric acid and 10 ml of ether and the mixture is warmed to room temperature. The phases are separated, the aqueous phase is extracted twice with ether and the combined organic phases are neutralized with saturated NaHCO3 solution. After drying over magnesium sulphate, the solvent is stripped off and the crude product of 500 mg weight is purified by chromatography on silica gel using ether/petroleum ether (1:3). 299 mg (64.6% of theory) of the title compound are obtained as a colorless liquid.

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted twice with ether
  3. dry with materialAfter drying over magnesium sulphate
  4. customthe crude product of 500 mg weight is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-69bb555cd5a04104ac91bbdee65fbdc5
Source dataset
uspto-grants-1993_06
Patent number
US05223633

Reaction notes

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