Isoamyl Nitrite → HCID 44376876, compound

HRID 1977031Notes

Reaction equation

HRID 1977031 reaction equation
F[C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C@H:8]2[CH2:24][N:12]3[CH2:13][CH2:14][N:15]([C:17]4[CH:22]=[CH:21][C:20](N)=[CH:19][CH:18]=4)[CH2:16][C@@H:11]3[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N(OCCC(C)C)=O>C1COCC1>[O:6]([CH2:7][C@H:8]1[CH2:24][N:12]2[CH2:13][CH2:14][N:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:16][C@@H:11]2[CH2:10][CH2:9]1)[C:5]1[CH:25]=[CH:26][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 54150949HCID 54150949, compound

Product 1

HCID 44376876HCID 44376876, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.400 g (1.13 mmol) of (7R,9aS)-7-(4-fluorophenoxy)methyl-2-(4-aminophenyl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine in 20 mL of THF was added dropwise to a solution of 0.33 mL (2.48 mmol) of isoamyl nitrite in 15 mL of THF. After the addition was complete, the solution was refluxed for 24 h. The solvent was evaporated, the residue dissolved in ethyl acetate, washed with 1 M sodium hydroxide (3×), washed with brine (1×), dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with ethyl acetate gave 0.060 g (16%) of the title compound. mp (—HCl) 247-252° C. HRMS calcd for C21H25FN2O: 340.1951, found: 340.1989.

Workup

  1. additionAfter the addition
  2. temperaturethe solution was refluxed for 24 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with 1 M sodium hydroxide (3×)
  6. washwashed with brine (1×)
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. customevaporated
  10. customPurification by flash silica gel chromatography with ethyl acetate

Sources & evidence

ORD record
ord-6f022d1a02cf4566926df7484e272813
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

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