Sodium borohydride → HCID 12834376, compound

HRID 1065276Notes

Reaction equation

HRID 1065276 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:31]#[N:32])[CH2:13][CH2:12][C:11]([N:14]3[CH2:30][CH2:29][C:17]4([N:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:20][NH:19][C:18]4=[O:28])[CH2:16][CH2:15]3)=[CH:10][CH2:9]2)=[CH:4][CH:3]=1.C[O-].[Na+].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:31]#[N:32])[CH2:9][CH2:10][CH:11]([N:14]3[CH2:30][CH2:29][C:17]4([N:21]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:20][NH:19][C:18]4=[O:28])[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 20540230HCID 20540230, compound

Product 1

HCID 12834376HCID 12834376, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 10.5 parts of 1-(4-fluorophenyl)-4-(4-oxo-1-phenyl-1,3,8-triazaspiro[4,5]dec-8-yl)-3-cyclohexene-1-carbonitrile, 1 part of sodium methoxide solution 30% and 320 parts of ethanol is added portionwise 1 part of sodium borohydride. Upon completion, starting at room temperature is continued for 6 hours. The reaction mixture is poured onto water and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of methanol and 2-propanone, yielding 3.2 parts of 1-(4-fluorophenyl)-4-(4-oxo-1-phenyl-1,3,8-triazaspiro[4,5]dec-8-yl)cyclohexanecarbonitrile; mp. 236.1° C.

Workup

  1. customstarting at room temperature
  2. additionThe reaction mixture is poured onto water
  3. extractionthe product is extracted with trichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and 5% of methanol as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is crystallized from a mixture of methanol and 2-propanone

Sources & evidence

ORD record
ord-e17712839098499c90149bc62218aef2
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

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