Methanol → HCID 23326057, compound

HRID 1980141Notes

Reaction equation

HRID 1980141 reaction equation
[Br-].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)([OH:23])[C:10]2[CH:15]=[CH:14][N+:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.CO.[BH4-].[Na+]>O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)([C:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH:11]=2)[OH:23])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 23326074HCID 23326074, compound

Product 1

HCID 23326057HCID 23326057, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 140.5 parts of 4-[bis(4-fluorophenyl)hydroxymethyl]-1-(phenylmethyl)pyridinium bromide in 640 parts of methanol were added portionwise, during a 2 hours-period, 15.1 parts of sodium borohydride at room temperature (cooling in ice-water was necessary). Upon completion, the whole was stirred and refluxed for 30 minutes. After cooling to room temperature, 800 parts of water were added. The whole was allowed to stand overnight. The reaction mixture was evaporated till all traces of methanol were removed. 1040 Parts of dichloromethane were added. The layers were separated. The organic layer was washed with 200 parts of water, dried, filtered and evaporated. The residue was taken up in dry methylbenzene and the whole was evaporated, yielding 111 parts (94.5%) of α,α-bis(4-fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinemethanol as an oily residue (intermediate 28).

Workup

  1. temperaturerefluxed for 30 minutes
  2. customThe reaction mixture was evaporated till all traces of methanol
  3. customwere removed
  4. addition1040 Parts of dichloromethane were added
  5. customThe layers were separated
  6. washThe organic layer was washed with 200 parts of water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customthe whole was evaporated

Sources & evidence

ORD record
ord-931aca6a77634e3da10285316aa6910e
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

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