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

HRID 887422ノート

反応式

HRID 887422 の反応式
[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

参加物

6

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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) +++++.

後処理

  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

出典と根拠

ORDレコード
ord-73db3d5b9a4142b8b037c902370fec10
出典データセット
uspto-grants-2012_08
特許番号
US08247418B2

反応ノート

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