Sodium borohydride → HCID 11539185, compound

HRID 2214959Notes

Reaction equation

HRID 2214959 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13](=[O:31])[CH:14]([CH2:27][N:28]([CH3:30])[CH3:29])[CH2:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[BH4-].[Na+]>CO>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]([OH:31])[CH:14]([CH2:27][N:28]([CH3:29])[CH3:30])[CH2:15][C:16]=2[C:17]2[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131725946HCID 131725946, compound

Product 1

HCID 11539185HCID 11539185, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 1.62 g of the 2-(4-tert-butylphenyl)-5-dimethylaminomethyl-3-(4-methanesulfonylphenyl)-cyclopent-2-enone, hydrochloride obtained according to Example 15 in 15 ml methanol was combined in portions with 0.40 g of sodium borohydride with stirring at a temperature of 20° C. Once addition was complete, the resultant reaction mixture was stirred for a further three hours and completely evaporated under reduced pressure. The residue was redissolved in 50 ml of distilled water and adjusted to a pH value of 11 with addition of potassium carbonate. Extraction was then performed three times with 20 ml portions of ethyl acetate and the combined extracts were washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated under reduced pressure. The resultant residue was purified by column chromatography on silica gel 60 (0.040–0.063 mm; E. Merck, Darmstadt, Germany) with a mixture of methanol and ethyl acetate in the ratio of 3:1 as eluent. 0.75 g of 2-(4-tert-butylphenyl)-5-dimethylaminomethyl-3-(4-methanesulfonylphenyl)-cyclopent-2-enol were obtained in the form of a colourless oil. This oil was redissolved in 25 ml of ethyl acetate and combined dropwise with stirring with 2 ml of a solution of hydrogen chloride in diethyl ether (5 wt. % HCl). A crystalline solid was obtained, which was isolated by suction filtration, washed with diethyl ether and dried under reduced pressure. 0.73 g of 2-(4-tert-butylphenyl)-5-dimethylaminomethyl-3-(4-methanesulfonylphenyl)-cyclopent-2-enol, hydrochloride (corresponding to 44.8% of theoretical) were obtained in the form of colourless crystals with a melting point of 223 to 224° C.

Workup

  1. additionOnce addition
  2. customthe resultant reaction mixture
  3. stirringwas stirred for a further three hours
  4. customcompletely evaporated under reduced pressure
  5. dissolutionThe residue was redissolved in 50 ml of distilled water
  6. additionadjusted to a pH value of 11 with addition of potassium carbonate
  7. extractionExtraction
  8. washthe combined extracts were washed with saturated sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. customevaporated under reduced pressure
  11. customThe resultant residue was purified by column chromatography on silica gel 60 (0.040–0.063 mm; E. Merck, Darmstadt, Germany) with a mixture of methanol and ethyl acetate in the ratio of 3:1 as eluent

Sources & evidence

ORD record
ord-4a2cef9364304bd885a97d608fe16fab
Source dataset
uspto-grants-2006_09
Patent number
US07109214B2

Reaction notes

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