Lithium Hexamethyldisilazide → HCID 67612488, compound

HRID 611794Notes

Reaction equation

HRID 611794 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10](=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:32]([C:34]1[CH:47]=[CH:46][C:37]([CH2:38][N:39]2[C:43]([CH:44]=[O:45])=[CH:42][N:41]=[CH:40]2)=[CH:36][CH:35]=1)#[N:33]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10](=[O:21])[CH:9]1[CH:44]([C:43]1[N:39]([CH2:38][C:37]2[CH:46]=[CH:47][C:34]([C:32]#[N:33])=[CH:35][CH:36]=2)[CH:40]=[N:41][CH:42]=1)[OH:45])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrileHCID 22254264HCID 22254264, compound

Product 1

HCID 67612488HCID 67612488, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the piperazinone from Step I (98.0 mg, 0.316 mmol) in 1.5 mL of THF at -78 ° C. was added dropwise 1M lithium hexamethyldisilazide solution (0.332 mL, 0.332 mmol). After 20 minutes. a solution of the aldehyde from Step E (76 mg, 0.360 mmol) in 0.5 mL of THF was added. After 30 min, the reaction was quenched with sat aq. NH4Cl soln., poured into EtOAc, and washed with sat. aq. NaHCO3 soln., and brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. The product was purified by flash chromatography on silica gel (3-6% MeOH/CH2Cl2) to provide 60 mg of the titled product as a 9:1 mixture of diastereomers.

Workup

  1. waitAfter 30 min
  2. customthe reaction was quenched with sat aq. NH4Cl soln
  3. addition, poured into EtOAc
  4. washwashed with sat. aq. NaHCO3 soln
  5. dry with materialThe solution was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide the crude product
  9. customThe product was purified by flash chromatography on silica gel (3-6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b389f27c809a40f7819f308a66b005df
Source dataset
uspto-grants-1999_12
Patent number
US06001835

Reaction notes

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