3,4,5,6-Tetrahydro-1H-1-benzazonine-2,7-dione → 7-Hydroxy-1,3,4,5,6,7-hexahydro-2H-1-benzazonin-2-one

HRID 2417843Notes

Reaction equation

HRID 2417843 reaction equation
[NH:1]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:15].[BH4-].[Na+]>C(O)C>[OH:14][CH:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:1][C:2](=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 5775413,4,5,6-Tetrahydro-1H-1-benzazonine-2,7-dioneHCID 4311764Sodium borohydride

Product 1

HCID 133387277-Hydroxy-1,3,4,5,6,7-hexahydro-2H-1-benzazonin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,4,5,6-tetrahydro-1H-(1)benzazonin-2,7-dione (14.2 g), J. Am. Chem. Soc. 88, 1049 (1966), and sodium borohydride (1.4 g) in ethanol (720 ml) is stirred at room temperature for 18 hours. The ethanol is removed under reduced pressure, and the residue dissolved in dichloromethane (350 ml). The solution is extracted with 2N hydrochloric acid (2×200 ml) and saturated brine (100 ml), and dried over sodium sulfate. The solvent is removed under reduced pressure to give 7-hydroxy-1,3,4,5,6,7-hexahydro-1-benzazonin-2-one.

Workup

  1. customThe ethanol is removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane (350 ml)
  3. extractionThe solution is extracted with 2N hydrochloric acid (2×200 ml) and saturated brine (100 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-595276d433bc49f1991e7bc3ffc12a5f
Source dataset
uspto-grants-1984_09
Patent number
US04470988

Reaction notes

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