m-Xylyl bromide → HCID 21193326, compound

HRID 443273Notes

Reaction equation

HRID 443273 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:23][CH2:22][CH:11]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:34][C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH2:38]Br>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:34][C:35]2[CH:42]=[CH:41][CH:40]=[C:37]([CH3:38])[CH:36]=2)([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:22][CH2:23]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 12099m-Xylyl bromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 222559134-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylate

Product 1

HCID 21193326HCID 21193326, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a cold (-78° C.) solution of benzyl N-tert-butoxycarbonyl-isonipecotate (8.02 g, 25.11 mmol) in anhydrous THF (80 mL), a solution of sodium bis(trimethysilyl)amide (35 mL, 35 mmol; 1M) in THF was added over a period of 10 min. The resulting orange solution was stirred at -78° C. for 1 h. and then treated dropwise with 3-methylbenzyl bromide (4.1 mL, 30.6 mmol). The reaction mixture was allowed to warm to room temp., and stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride, diluted with water, and extracted with ethyl acetate. The organic extracts were combined, washed with brine, and concentrated under vacuum. The residual oil was subjected to column chromatography on silica eluting with 20% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title product.

Workup

  1. temperatureto warm to room temp.
  2. stirringstirred overnight
  3. customThe reaction was quenched with saturated aqueous ammonium chloride
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. concentrationconcentrated under vacuum
  8. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-f64c3a42dfd44820bd1b4599428ee5a2
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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