Ethyl Acetate → HCID 18782335, compound

HRID 1420650Notes

Reaction equation

HRID 1420650 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[C:13]1([N:19]2[C:23]3([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:22](=[O:29])[NH:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([BH3-])#N.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1COCC1.CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([N:26]1[CH2:25][CH2:24][C:23]3([N:19]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:20][NH:21][C:22]3=[O:29])[CH2:28][CH2:27]1)[CH2:6][CH2:5]2

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 44561396-Chloro-2-tetraloneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18782335HCID 18782335, compoundYield 81.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-2-tetralone (22.7 mmol) was dissolved in toluene (210 ml). 1-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one (22.7 mmol) and molecular sieves (10 g) were added and the mixture was refluxed for 6 h. After cooling the molecular sieves were removed by filtration and washed with methylene chloride. Evaporation of the filtrate yielded a residue which was dissolved in THF (90 ml) and methanol (10 ml). Sodium cyanoborohydride (22.7 mmol) was added to the solution and the pH was adjusted to 4. The mixture was stirred for 4 h at room temperature. Ethyl acetate was added and the organic phase was washed with 2 N sodium hydroxide and brine. The organic phase was concentrated and chromatographed over silica gel (ethyl acetate). Addition of HCl in ethanol to a solution of the product in ethyl acetate/ethanol yielded 8-(6-chloro-1,2,3,4-tetrahydro-2-naphthyl)-1-phenyl-1,3,8-triaza--spiro[4.5]decan-4-one hydrochloride (4.0 g, 41%) as colorless solid, m.p. 288-290° C.

Workup

  1. temperaturethe mixture was refluxed for 6 h
  2. temperatureAfter cooling the molecular sieves
  3. customwere removed by filtration
  4. washwashed with methylene chloride
  5. customEvaporation of the filtrate
  6. customyielded a residue which
  7. washthe organic phase was washed with 2 N sodium hydroxide and brine
  8. concentrationThe organic phase was concentrated
  9. customchromatographed over silica gel (ethyl acetate)
  10. additionAddition of HCl in ethanol to a solution of the product in ethyl acetate/ethanol

Sources & evidence

ORD record
ord-ad171d790de24624bf889ebcf3155229
Source dataset
uspto-grants-2000_06
Patent number
US06071925

Reaction notes

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