Potassium sodium tartarate → 6-Chloro-7-ethoxy-4-methyl-1,2,3,4-tetrahydro-2,4a,5-triaza-fluorene

HRID 1272102Notes

Reaction equation

HRID 1272102 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:12](=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[CH:11]=[C:10]1[N:5]2[C@H:6]([CH3:19])[CH2:7][NH:8][C:9]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>COC(C)(C)C>[Cl:1][C:2]1[N:3]=[C:4]2[C:12](=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[CH:11]=[C:10]1[N:5]2[CH:6]([CH3:19])[CH2:7][NH:8][CH2:9]1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 86596342(R)-6-chloro-7-ethoxy-4-methyl-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one

Product 1

HCID 184559876-Chloro-7-ethoxy-4-methyl-1,2,3,4-tetrahydro-2,4a,5-triaza-fluorene

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A suspension consisting of 0.51 g (1.82 mmol) (R)-6-chloro-7-ethoxy-4-methyl-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one and 0.28 g (7.30 mmol) lithium aluminium hydride in 10 mL tert-butyl methyl ether was heated at reflux for 1 h. After cooling to room temperature the reaction mixture was poured into 10% aqueous sodium potassium tartrate solution and extracted twice with ethyl acetate. The organic fractions were washed with brine, dried over magnesium sulfate, filtered and evaporated. The so-obtained crude 6-chloro-7-ethoxy-4-methyl-1,2,3,4-tetrahydro-2,4a,5-triaza-fluorene was dissolved in 10 mL dichloromethane and 0.48 g (2.19 mmol) di-tert-butyl dicarbonate and 22.3 mg (0.18 mmol) 4-(dimethylamino)pyridine were added. After 1 h the solvent was evaporated and the residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:4) as eluant to give the product as a light yellow solid (63.9%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. extractionextracted twice with ethyl acetate
  4. washThe organic fractions were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-eadc1d850cc74837b58a075cc6f9043c
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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