Ammonium Chloride → (Rac)-trans-3-(3-fluoropyrazin-2-yl)cyclohexanol

HRID 555835Notes

Reaction equation

HRID 555835 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:5]([C:10]2[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH:11]=2)=[N:6][CH:7]=[CH:8][N:9]=1.[Cl-].[NH4+]>CO>[F:3][C:4]1[C:5]([C@@H:10]2[CH2:15][CH2:14][CH2:13][C@H:12]([OH:16])[CH2:11]2)=[N:6][CH:7]=[CH:8][N:9]=1.[F:3][C:4]1[C:5]([C@H:10]2[CH2:15][CH2:14][CH2:13][C@H:12]([OH:16])[CH2:11]2)=[N:6][CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 593514053-(3-Fluoropyrazin-2-yl)cyclohex-2-enone

Product 2

HCID 59351407(Rac)-trans-3-(3-fluoropyrazin-2-yl)cyclohexanolHCID 66986535(Rac)-cis-3-(3-fluoropyrazin-2-yl)cyclohexanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (295 mg, 7.80 mmol) was added was added portion wise to a solution of 3-(3-fluoropyrazin-2-yl)cyclohex-2-enone (500 mg, 2.60 mmol) in MeOH (15 ml) at RT. After completion of the addition the reaction mixture was stirred at RT for 30 minutes. It was then cooled in an ice-water bath, saturated aqueous ammonium chloride (25 ml) was added dropwise, and the resulting mixture was extracted with EtOAc (2×100 ml). The combined organic layers were washed with brine and dried over sodium sulfate. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (0% to 20% EtOAc in hexanes) afforded (rac)-cis-3-(3-fluoropyrazin-2-yl)cyclohexanol and (rac)-trans-3-(3-fluoropyrazin-2-yl)cyclohexanol as colorless oils. MS (ESI, pos. ion) m/z: 197.0 (M+1) and MS (ESI, pos. ion) m/z: 197.0 (M+1), respectively. IC50 (uM) +++++.

Workup

  1. additionAfter completion of the addition the reaction mixture
  2. temperatureIt was then cooled in an ice-water bath
  3. extractionthe resulting mixture was extracted with EtOAc (2×100 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-24d808d2ad284a8ab52eb203640aea9a
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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