Sodium Bicarbonate → HCID 69309358, compound

HRID 2054565Notes

Reaction equation

HRID 2054565 reaction equation
[C:1]([CH:5]1[CH2:12][CH2:11][CH2:10][NH:9][C:8](=[O:13])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].F[B-](F)(F)F.[CH3:19][O+](C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([CH:5]1[CH2:6][CH2:7][C:8]([O:13][CH3:19])=[N:9][CH2:10][CH2:11][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 69312820HCID 69312820, compound

Product 1

HCID 69309358HCID 69309358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-tert-Butylazocan-2-one (30 mg) was dissolved in 2 mL methylene chloride and stirred at room temperature under nitrogen. 31.3 g Trimethyloxonium tetrafluoroborate was added and the reaction stirred overnight. The mixture was added to saturated aqueous sodium bicarbonate and extracted with methylene chloride (2×). The combined organic layers were washed with brine, dried over magnesium sulfate, and the solvent evaporated to provide crude 5-tert-butyl-8-methoxy-2,3,4,5,6,7-hexahydroazocine.

Workup

  1. stirringthe reaction stirred overnight
  2. extractionextracted with methylene chloride (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-c82de5be4a37489e8a78f7b2cd97ac4c
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Reaction notes

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