Sodium borohydride → [6-[2-(3-Methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]methanol

HRID 2194897노트

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HRID 2194897 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[C:15]([C:16](OC)=[O:17])=[CH:14][N:13]=1.[BH4-].[Na+]>CO.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:13]=[CH:14][C:15]([CH2:16][OH:17])=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:21]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 67447798Methyl 6-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)nicotinate

생성물 1

HCID 67448255[6-[2-(3-Methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]methanol

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

To a solution of methyl 6-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)nicotinate (1 eq.) from step 1, in MeOH (0.14M) was added portion wise sodium borohydride (9.3 eq.). The mixture was stirred at 65° C. for 12 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel, eluting with Hex/EtOAc 20% afforded the desired compound as an oil.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel
  9. washeluting with Hex/EtOAc 20%

출처 및 근거

ORD 기록
ord-709134f9f9724bd6b5db0381c8e33ee6
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334308B2

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