Ethyl Acetate → 8-[(1H-Inden-2-yl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

HRID 2072505Notes

Reaction equation

HRID 2072505 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([N:12]1[CH2:28][CH2:27][C:15]2([N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][NH:17][C:16]2=[O:26])[CH2:14][CH2:13]1)=O.[BH4-].[Na+].C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC>N1C=CC=CC=1>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:1]=[C:2]1[CH2:10][N:12]1[CH2:28][CH2:27][C:15]2([N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][NH:17][C:16]2=[O:26])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 214082488-(1H-Indene-2-carbonyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

Product 1

HCID 214081988-[(1H-Inden-2-yl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-oneYield 11.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Crude 8-(1H-inden-2-ylcarbonyl)-1-phenyl-1,3,8-triazaspiro-[4.5]decan-4-one (11.4g) is dissolved in dry pyridine (250 ml), treated with sodium borohydride (6.0g), and the resulting mixture is refluxed for 16 hours under a nitrogen atmosphere. The pyridine solution is cooled, poured into 2 liters of ice water, stirred for 1 hour and the precipitates filtered off. The crude product is dissolved in chloroform and washed with water and saturated sodium bicarbonate solution. Concentration of the dried chloroform solution gives a crude solid which is a mixture of compounds. Column chromatography through silica gel using ethyl acetate followed by high pressure liquid chromatography with 4:1 ethyl acetate/hexane gives 1.3g of the title compound, melting point 184°14 186° C.

Workup

  1. temperaturethe resulting mixture is refluxed for 16 hours under a nitrogen atmosphere
  2. filtrationthe precipitates filtered off
  3. dissolutionThe crude product is dissolved in chloroform
  4. washwashed with water and saturated sodium bicarbonate solution
  5. customConcentration of the dried chloroform solution gives a crude solid which
  6. additiona mixture of compounds

Sources & evidence

ORD record
ord-9507ea2b267e45038592f5930a152400
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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