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o-Xylyl bromide → HCID 54269290, compound

HRID 1068414
Notes
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Reaction equation

HRID 1068414 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37]Br>C1COCC1>[CH2:1]([O:8][C:9](=[O:23])[C:10]1([CH2:34][C:35]2[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=2[CH3:37])[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6992o-Xylyl bromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 222559134-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylate

Product 1

HCID 54269290HCID 54269290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of N-t-butoxycarbonyl isonipecotic acid benzyl ester (13.34 g, 41.8 mmol) in THF (100 ml) at −78° C. was added sodium bis-trimethysilylamide (59 ml of a 1.0 M THF solution, 59 mmol) over 15 min. The resulting orange solution was stirred at −78° C. for 1 hr and then treated dropwise with 2-methyl benzyl bromide (6.80 ml, 50.7 mmol) and then allowed to warm slowly to room temperature over 16 hrs. The reaction was quenched with saturated aqueous NH4Cl, diluted with H2O, and extracted with EtOAc. The combined organic extracts were washed with brine, and concentrated in vacuo to an orange gum. Chromatography (SiO2, gradient elution, 20 to 30% EtOAc in hexanes) afforded the product as a white solid.

Workup

  1. temperatureto warm slowly to room temperature over 16 hrs
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. additiondiluted with H2O
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. concentrationconcentrated in vacuo to an orange gum
  7. washChromatography (SiO2, gradient elution, 20 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2c0de00953e74274a67d25d903d67a07
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06248756B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes