Sodium borohydride → Ethyl 2-[4-(2-{[5-(hydroxymethyl)pyridin-2-yl][4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate

HRID 2251538노트

반응식

HRID 2251538 반응식
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=2)[CH2:10][CH2:11][C:12]2[CH:26]=[CH:25][C:15]([O:16][C:17]([CH3:24])([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][C:35]([F:38])([F:36])[F:37])=[CH:32][CH:33]=2)[CH2:10][CH2:11][C:12]2[CH:26]=[CH:25][C:15]([O:16][C:17]([CH3:23])([CH3:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=2)=[N:7][CH:8]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 59643273Ethyl 2-[4-(2-{(5-formylpyridin-2-yl)[4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate

생성물 1

HCID 69099388Ethyl 2-[4-(2-{[5-(hydroxymethyl)pyridin-2-yl][4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate수율 89.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of ethyl 2-[4-(2-{(5-formylpyridin-2-yl)[4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (500 mg; 0.94 mmol) in 7 ml of methanol was cooled in an ice bath and treated with sodium borohydride (65 mg; 1.7 mmol) in small portions. After 30 minutes, the reaction mixture was concentrated and the residue partitioned between ethyl acetate and saturated brine. The organic phase was washed with water and the combined aqueous phases reextracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. Purification by radial chromatography using ethyl acetate-hexane mixtures (5–50% gradient) afforded ethyl 2-[4-(2-{[5-(hydroxymethyl)pyridin-2-yl][4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (450 mg; 85% yield).

후처리

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and saturated brine
  3. washThe organic phase was washed with water
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by radial chromatography

출처 및 근거

ORD 기록
ord-3ceceb6dbe31453aa4d411f0b598b588
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07319104B2

반응 노트

불러오는 중…