m-Xylyl bromide → HCID 53993375, compound

HRID 1068444Notes

Reaction equation

HRID 1068444 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:34]=[CH:35][CH:36]=1)[CH2:32]Br>C1COCC1>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:4]([CH2:28][C:29]2[CH:36]=[CH:35][CH:34]=[C:31]([CH3:32])[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

5

Reactant 3

HCID 12099m-Xylyl bromideHCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 53993375HCID 53993375, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (−78° C.) solution of methyl N-tert-butoxycarbonyl-piperidine-4-carboxylate (5.0 g, 20.5 mmol; Example 3, Step B) in anhydrous THF (70 mL), a solution of sodium bis(trimethylsilyl)amide (20.5 mL, 1M, 20.5 mmol) was added over a period of 30 min. The resultant mixture was stirred at −78° C. for 1 h., and 3-methylbenzyl bromide (2.77 mL, 20.5 mmol) was added. The reacting mixture was allowed to warm up to room temp. and stirred overnight. The product mixture was concentrated, and the residue was partitioned between water and ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 10% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. temperatureto warm up to room temp.
  2. concentrationThe product mixture was concentrated
  3. customthe residue was partitioned between water and ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-b437397f97b84cb69edfc4c04c9c79d3
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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