Sodium bis(trimethylsilyl)amide → HCID 69843273, compound

HRID 1634236Notes

Reaction equation

HRID 1634236 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1[NH:7][C:8](=[O:30])[C:9]2[C:10]3[N:19]([CH3:20])[C:18]([NH:21][C:22]4[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:29])=[N:17][C:11]=3[CH:12]=[CH:13][C:14]=2[C:15]=1[CH3:16].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:29])[C:22]=1[NH:21][C:18]1[N:19]([CH3:20])[C:10]2[C:9]3[C:8](=[O:30])[NH:7][C:6]([CH:5]=[CH:4][CH2:3][OH:2])=[C:15]([CH3:16])[C:14]=3[CH:13]=[CH:12][C:11]=2[N:17]=1

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 21226445Aluminium lithium hydrideHCID 69843388HCID 69843388, compound

Product 1

HCID 69843273HCID 69843273, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A suspension of the product of Example 12 (100 mg, 0.22 mmol) in THF (7 mL) was cooled to −78° C. Sodium bis(trimethylsilyl)amide (1M in THF, 0.44 mmol) was added dropwise. The bright red solution was warmed to 0° C. for 15 minutes, then lithium aluminum hydride (1M in THF, 2.6 mmol) was added and the orange solution was warmed to room temperature for 0.5 h. The mixture was cooled to 0° C., quenched with saturated ammonium chloride and extracted with ethyl acetate. Column chromatography (3-6% MeOH—CH2Cl2) provided the title compound (32 mg, 34%), mp 298-300° C.; MS(ES) 429, 431 (MH+).

Workup

  1. temperatureThe bright red solution was warmed to 0° C. for 15 minutes
  2. temperaturethe orange solution was warmed to room temperature for 0.5 h
  3. temperatureThe mixture was cooled to 0° C.
  4. customquenched with saturated ammonium chloride
  5. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-eff71560145e43668b96445974c5de76
Source dataset
uspto-grants-2003_01
Patent number
US06506769B2

Reaction notes

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