Diethyl Ether → HCID 20158213, compound

HRID 986228Notes

Reaction equation

HRID 986228 reaction equation
C(OCC)C.[H-].[Na+].[CH2:8]([O:10][C:11]([C:13]1[NH:14][C:15]2[CH2:16][N:17]([C:22](=[O:24])[CH3:23])[CH2:18][CH2:19][C:20]=2[CH:21]=1)=[O:12])[CH3:9].[C:25]([O:29][C:30](=O)[O:31]C(C)(C)C)([CH3:28])([CH3:27])[CH3:26]>CN(C)C=O>[C:25]([O:29][C:30]([N:14]1[C:15]2[CH2:16][N:17]([C:22](=[O:24])[CH3:23])[CH2:18][CH2:19][C:20]=2[CH:21]=[C:13]1[C:11]([O:10][CH2:8][CH3:9])=[O:12])=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 20158231HCID 20158231, compound

Product 1

HCID 20158213HCID 20158213, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A suspension of diethyl ether washed sodium hydride (0.28 g, 0.009 mole) in dry dimethylformamide (8 ml) at 0° C. was treated with a solution of 2-ethoxycarbonyl-6-acetyl-4,5,6,7-tetrahydro-6-azaindole from Example 2 (2 g, 0.0085 mole) in dry dimethylformamide (2 ml) and stirred for 20 minutes. The mixture was warmed to room temperature and stirred for 1 hour by which time solution was complete. The solution was cooled to 0° C., a solution of di-tert-butylcarbonate (1.85 g, 0.0085 mole) in dry dimethylformamide (2 ml) added dropwise over 10 minutes, and the solution stirred at room temperature for 4 hours. The mixture was quenched with water (200 ml), extracted with ethyl acetate (4×100 ml) the organic extracts washed with brine (3×100 ml), dried over sodium sulphate, and evaporated to give a yellow oil which was chromatographed on silica gel (20 g) eluting with dichloromethane:hexane (9:1) to give the title product as a pale yellow oil (1.4 g, 49%). Found: C, 60.12; H, 7.32; N, 8.15. C17H24N2O5 requires C, 60.70; H, 7.19; N, 8.33%.

Workup

  1. stirringstirred for 1 hour by which time solution
  2. temperatureThe solution was cooled to 0° C.
  3. stirringthe solution stirred at room temperature for 4 hours
  4. customThe mixture was quenched with water (200 ml)
  5. extractionextracted with ethyl acetate (4×100 ml) the organic extracts
  6. washwashed with brine (3×100 ml)
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customto give a yellow oil which
  10. customwas chromatographed on silica gel (20 g)
  11. washeluting with dichloromethane:hexane (9:1)

Sources & evidence

ORD record
ord-bb771cca00d9402c8b07833c94f0bb4f
Source dataset
uspto-grants-1987_12
Patent number
US04711882

Reaction notes

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