Water → HCID 15573078, compound

HRID 1733224Notes

Reaction equation

HRID 1733224 reaction equation
[C:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]([O:18]C(=O)C)=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)(OC)=[O:2].[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1>[OH:2][CH2:1][C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]([OH:18])=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

5

Reactant 3

HCID 962WaterHCID 15593372HCID 15593372, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15573078HCID 15573078, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of dry tetrahydrofuran were dissolved 70 mg of the product of 1-carbomethoxy-4-acetoxy-9H-pyrido[3,4-b]indole. With ice-cooling, 4.0 ml of diisobutylaluminum hydride were added. The reaction mixture was allowed to stand for 2 hours, after which the unreacted reagent was decomposed with a small amount of water. The mixture was then extracted with ethyl acetate. The organic layers were pooled and concentrated and the resultant crystals were recrystallized from ethyl acetate to yield 16 mg of the title compound as white needles melting at 148°-150°0 C. (decomp.). The IR absorption spectrum shows absorption at 1680 cm-1 has disappeared. An intense absorption was observed at 1620 cm-1. Mol. wt. (based on mass spectrum) 214.

Workup

  1. temperatureWith ice-cooling
  2. extractionThe mixture was then extracted with ethyl acetate
  3. concentrationconcentrated
  4. customthe resultant crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a923435638644a17ae6ff96dd24d3373
Source dataset
uspto-grants-1980_12
Patent number
US04241064

Reaction notes

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