Benzaldehyde → 3-(3-(Benzylamino)phenyl)-3-hydroxypropanenitrile

HRID 1189974노트

반응식

HRID 1189974 반응식
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]([OH:26])[CH2:23][C:24]#[N:25])[CH:19]=[CH:20][CH:21]=1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:27]([NH:15][C:16]1[CH:17]=[C:18]([CH:22]([OH:26])[CH2:23][C:24]#[N:25])[CH:19]=[CH:20][CH:21]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 593169603-(3-Aminophenyl)-3-hydroxypropanenitrile

생성물 1

HCID 672967283-(3-(Benzylamino)phenyl)-3-hydroxypropanenitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

NaBH(OAc)3 (7.84 g, 36.99 mmol) was added to a solution of aniline 12 (2.0 g, 12.33 mmol) and benzaldehyde (1.3 g, 12.33 mmol) in DCM. The resulting mixture was stirred at RT for 5 h and quenched with saturated aqueous NaHCO3. Organic layer was washed with water followed by brine and dried over anhydrous Na2SO4. Organic layer was concentrated under reduced pressure. Purification by flash chromatography (40% to 50% EtOAc—hexanes gradient) gave 3-(3-(benzylamino)phenyl)-3-hydroxypropanenitrile as a pale yellow oil. Yield (2.61 g, 83%); 1H NMR (400 MHz, DMSO-d6) δ 7.36-7.29 (m, 4H), 7.23-7.19 (m, 1H), 6.99 (t, J=8.0 Hz, 1H), 6.68 (s, 1H), 6.54 (d, J=7.6 Hz, 1H), 6.44 (dd, J=1.6, 8.0 Hz, 1H), 6.27 (t, J=6.0 Hz, 1H), 5.79 (d, J=4.4 Hz, 1H), 4.72-4.68 (m, 1H), 4.25 (d, J=6.0 Hz, 2H), 2.82-2.67 (m, 2H).

후처리

  1. customquenched with saturated aqueous NaHCO3
  2. washOrganic layer was washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationOrganic layer was concentrated under reduced pressure
  5. customPurification by flash chromatography (40% to 50% EtOAc—hexanes gradient)

출처 및 근거

ORD 기록
ord-d23508e709144268b55764c700c95fb6
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674137B2

반응 노트

불러오는 중…