3-Methylbenzoyl chloride → HCID 54052971, compound

HRID 1068475Notes

Reaction equation

HRID 1068475 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](Cl)=[O:33]>C1COCC1.C(OCC)(=O)C>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:4]([C:32](=[O:33])[C:31]2[CH:35]=[CH:36][CH:37]=[C:29]([CH3:28])[CH:30]=2)([C:3]([O:2][CH3:1])=[O:17])[CH2:5][CH2:6]1)=[O:11])([CH3:14])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 743753-Methylbenzoyl chlorideHCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 54052971HCID 54052971, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (−78° C.) solution of methyl N-tert-butoxycarbonyl-piperidine-4-carboxylate (0.25 g, 1.03 mmol; Example 3, Step B) in anhydrous THF (10 mL), a solution of sodium bis(trimethylsilyl)amide (1.2 mL, 1M, 1.2 mmol) was added over a period of 5 min. The resultant mixture was stirred at −78° C. for 1 h., and 3-methylbenzoyl chloride (135 μL, 1.02 mmol) was added. The reacting mixture was allowed to warm up to room temp. and stirred overnight. The product mixture was diluted with ethyl acetate and washed with brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 8-10% ethyl acetate in hexane gradient. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. temperatureto warm up to room temp.
  2. washwashed with brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-20caa95f163542f8a0e27f6d2954a3ed
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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