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o-Xylyl bromide → HCID 54269290, compound

HRID 1901076
Notes
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Reaction equation

HRID 1901076 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+].Br[CH2:35][C:36]1[C:37]([CH3:42])=[CH:38][CH:39]=[CH:40][CH:41]=1>C1COCC1>[CH2:1]([O:8][C:9](=[O:23])[C:10]1([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[CH3:42])[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 cold (-78° C.) solution of N-t-butoxycarbonyl isonipecotic acid benzyl ester (13.34 g, 41.8 mmol) in 140 ml of dry THF was added a 1.0 M THF solution of sodium bis trimethysilylamide (59 ml, 59 mmol) over 15 min. The resulting orange solution was stirred at -78° C. for 1 h and then treated dropwise with α-bromo-o-xylene (6.8 ml, 50.7 mmol) and then allowed to warm slowly to room temp. overnight. The reaction was quenched with saturated aqueous NH4Cl, diluted with H2O, and extracted with EtOAc (2×). The combined organic extracts were washed with brine (2×), and concentrated in vacuo to an orange gum. Flash chromatography on silica with 20% to 30% EtOAc/hexane as eluent, combining appropriate fractions, and concentrating in vacuo, afforded the product as a white solid.

Workup

  1. temperatureto warm slowly to room temp. overnight
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. additiondiluted with H2O
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic extracts were washed with brine (2×)
  6. concentrationconcentrated in vacuo to an orange gum
  7. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-73fe703b86404613b9048af86ee66577
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05576313

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes