Tert-Butyl nitrite → HCID 136404655, compound

HRID 1359024Notes

Reaction equation

HRID 1359024 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1.CC(C)([O-])C.[K+].[N:19](OC(C)(C)C)=[O:20]>C1COCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[N:19][OH:20])[C:11]=2[CH:12]=1

Participants

6

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 18180253HCID 18180253, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 136404655HCID 136404655, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 3-methoxy-5,6,7,8-tetrahydroisoquinoline (1.40 g, 8.59 mmol) in THF (20 ml) was added to a solution of potassium tert-butoxide (1.92 g, 17.18 mmol) in THF (25 ml) and the resulting mixture was stirred at room temperature for 18 h, then cooled to 0° and tert-butyl nitrite (3.05 ml, 2.65 g, 27.77 mmol) added dropwise. After stirring for 18 h at room temperature brine was added and the mixture extracted three times with ethyl acetate. The combined organic phase was dried (MgSO4) and concentrated to afford the title compound (1.50 g) as a flesh coloured solid m.p. 175-178° MS (ES+) 193 (MH+).

Workup

  1. temperaturecooled to 0°
  2. additionwas added
  3. extractionthe mixture extracted three times with ethyl acetate
  4. dry with materialThe combined organic phase was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2e10e63787f046aa9d6fbc604aadbe8f
Source dataset
uspto-grants-2003_07
Patent number
US06599908B1

Reaction notes

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