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Sodium hydride → 1-(tert-Butoxycarbonyl)-2-ethoxycarbonyl-6-(2,2,2-trichloroethoxycarbonyl)-4,5,6,7-tetrahydro-6-azaindole

HRID 986227
Notes
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Reaction equation

HRID 986227 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[CH2:11][N:12]([C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[CH2:13][CH2:14][C:15]=2[CH:16]=1)=[O:7])[CH3:4].[H][H].[C:27]([O:31][C:32](=O)[O:33]C(C)(C)C)([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O.O.C(OCC)C>[C:27]([O:31][C:32]([N:9]1[C:10]2[CH2:11][N:12]([C:17]([O:19][CH2:20][C:21]([Cl:23])([Cl:24])[Cl:22])=[O:18])[CH2:13][CH2:14][C:15]=2[CH:16]=[C:8]1[C:6]([O:5][CH2:3][CH3:4])=[O:7])=[O:33])([CH3:30])([CH3:29])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 201582272-Ethoxycarbonyl-6-(2,2,2-trichloroethoxycarbonyl)-4,5,6,7-tetrahydro-6-azaindoleHCID 178418361HCID 178418361, compound

Product 1

HCID 201582331-(tert-Butoxycarbonyl)-2-ethoxycarbonyl-6-(2,2,2-trichloroethoxycarbonyl)-4,5,6,7-tetrahydro-6-azaindole
Yield 90.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

A suspension of diethyl ether washed sodium hydride (1.22 g, 0.041 mole) in dry dimethylformamide (50 ml) under nitrogen at 0° C. was treated with a solution of 2-ethoxycarbonyl-6-(2,2,2-trichloroethoxycarbonyl)-4,5,6,7-tetrahydro-6-azaindole from Example 3 (13.4 g, 0.036 mole) in dry dimethylformamide (35 ml) dropwise over 10 minutes. Evolution of hydrogen was noted and the mixture stirred at room temperature for 10 minutes. The solution was cooled to 0° C. and treated dropwise with a solution of di-tert-butylcarbonate (8.94 g, 0.041 mole) in dry dimethylformamide (25 ml) over 10 minutes. The mixture was allowed to stand at room temperature overnight, water (100 ml) added and the resulting solution evaporated under vacuum to low bulk. The residue was diluted with water (200 ml) extracted with ethyl acetate (4×100 ml) the combined extracts washed with water (50 ml) and brine (3×100 ml), dried over sodium sulphate and evaporated to give a brown viscous oil, which was chromatographed on silica gel (250 g) eluting with hexane:dichloromethane (2:1), followed by dichloromethane to give the title product as a pure viscous oil (15.3 g, 80%). Found: C, 46.42; H, 5.08; N, 5.72. C18H23Cl3N2O6 requires C, 46.02; H, 4.93; N, 5.96%.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. waitto stand at room temperature overnight
  3. customthe resulting solution evaporated under vacuum to low bulk
  4. additionThe residue was diluted with water (200 ml)
  5. extractionextracted with ethyl acetate (4×100 ml) the combined extracts
  6. washwashed with water (50 ml) and brine (3×100 ml)
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customto give a brown viscous oil, which
  10. customwas chromatographed on silica gel (250 g)
  11. washeluting with hexane:dichloromethane (2:1)

Sources & evidence

ORD record
ord-49d17cbf23d740bdb73117dfa903a005
Source dataset
uspto-grants-1987_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04711882

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes