Sodium borohydride → 10-Hydroxy-4-methoxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine

HRID 1576271Notes

Reaction equation

HRID 1576271 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:23])[C:10]3[C:15]([C:16]4([CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3.[BH4-].[Na+]>C(O)C.O>[OH:23][CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2([CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]1=2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 867339644-Methoxy-1'-methyl-10-oxo-9,10-dihydroanthracene-9-spiro-4'-piperidine

Product 1

HCID 8673396310-Hydroxy-4-methoxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Methoxy-1'-methyl-10-oxo-9,10-dihydroanthracene-9-spiro-4'-piperidine (1.8 g.), in ethanol (100 ml.) is treated with sodium borohydride (2 g.), allowed to stand at room temperature overnight, then the reaction mixture is diluted with water and extracted with ether. The ether is washed with water, dried (MgSO4) and evaporated to give an oil which is chromatographed on magnesium silicate. Elution with toluene-ethyl acetate gives 10-hydroxy-4-methoxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine, m.p. 149°-151°C. on recrystallisation from aqueous ethanol.

Workup

  1. extractionextracted with ether
  2. washThe ether is washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an oil which
  6. customis chromatographed on magnesium silicate
  7. washElution with toluene-ethyl acetate

Sources & evidence

ORD record
ord-6a6a68e9d53a454b9e38ae89110353d4
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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