HCID 58409382, compound → HCID 178448797, compound

HRID 386978Notes

Reaction equation

HRID 386978 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]1[C:15](=O)[CH2:16][CH2:17][CH2:18][CH:19]=1)([CH3:3])[CH3:2]>C(N[Ti])CCC.C1(C)C=CC=CC=1>[CH2:5](/[N:13]=[C:15]1\[CH2:16][CH2:17][CH2:18][CH:19]=[C:14]\1[NH:13][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11])[CH2:4][CH2:1][CH3:2]

Participants

4

Reactant 1

HCID 58409382HCID 58409382, compound

Product 1

HCID 178448797HCID 178448797, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 178449866HCID 178449866, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

The r indicates a number of repeat units of Ti(N(n-Bu)2. Reaction is set up in a glove box under N2 atmosphere. A 20-mL vial equipped with a stir bar is charged with (0.4858 g, 1.7900 mmol) of 2-(2,6-diisopropylphenylamino)cyclohex-2-enone (Preparation 3), toluene (6.0 mL) and (0.3022 g, 0.8984 mmol) of polymeric n-butylamino-titanium reagent (Preparation 4). The mixture is stirred overnight (24 hours). 1H-NMR of aliquot showed reaction is not complete. About 26% of starting material remained. Therefore, to the mixture are added 46.2 mg of polymeric n-butylamino-titanium reagent (Preparation 4). After stirring overnight, 1H-NMR of aliquot showed that no starting material remained. To the mixture are added hexanes, and the resulting mixture is filtered. Hexanes are also used to wash filtercake solids. The filtrate (yellow solution) is concentrated under reduced pressure to afford 305.8 mg (52.3%) of compound (B) of Example B as a yellow oil.

Workup

  1. customReaction
  2. customis set up in a glove box under N2 atmosphere
  3. customA 20-mL vial equipped with a stir bar
  4. custom1H-NMR of aliquot showed reaction
  5. stirringAfter stirring overnight
  6. filtrationthe resulting mixture is filtered
  7. washto wash filtercake solids
  8. concentrationThe filtrate (yellow solution) is concentrated under reduced pressure

Sources & evidence

ORD record
ord-9d5b9fce23bb414490e80414dee6f754
Source dataset
uspto-grants-2013_02
Patent number
US08372927B2

Reaction notes

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