Sodium borohydride → 3-Hydroxy-3-(3-(5-methoxypentylamino)phenyl)propanenitrile

HRID 1189951노트

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HRID 1189951 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=O.[NH2:9][C:10]1[CH:11]=[C:12]([CH:16]([OH:20])[CH2:17][C:18]#[N:19])[CH:13]=[CH:14][CH:15]=1.[BH4-].[Na+]>CO>[OH:20][CH:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:11]=1)[CH2:17][C:18]#[N:19]

참가 물질

5

반응물 3

HCID 4311764Sodium borohydrideHCID 130279335-MethoxypentanalHCID 593169603-(3-Aminophenyl)-3-hydroxypropanenitrile

생성물 1

HCID 672967943-Hydroxy-3-(3-(5-methoxypentylamino)phenyl)propanenitrile

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 5-methoxypentanal (0.644 g, 5.54 mmol), 3-(3-aminophenyl)-3-hydroxypropanenitrile (12) (1.0 g, 6.16 mmol) and activated molecular sieves in methanol was stirred at RT for 8 hrs. NaBH4 (0.937 g, 24.6 mmol) was added portion wise to the reaction mixture at 0° C. The reaction mixture was stirred at RT overnight. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. Purification by column chromatography (100-200 silica, 0% to 70% EtOAc—hexanes gradient) gave 3-hydroxy-3-(3-(5-methoxypentylamino)phenyl)propanenitrile as a yellow oil. Yield (0.34 g, 21%); 1H NMR (400 MHz, CDCl3) δ 7.17 (t, J=8.0 Hz, 1H), 6.66 (d, J=7.6 Hz, 1H), 6.62 (s, 1H), 6.56 (d, J=8.0 Hz, 1H), 4.95 (t, J=6.4 Hz, 1H), 3.39 (t, J=6.4 Hz, 2H), 3.33 (s, 3H), 3.12 (t, J=7.2 Hz, 2H), 2.75 (d, J=6.4 Hz, 2H), 1.68-1.59 (m, 4H), 1.51-1.43 (m, 2H).

후처리

  1. stirringThe reaction mixture was stirred at RT overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customPurification by column chromatography (100-200 silica, 0% to 70% EtOAc—hexanes gradient)

출처 및 근거

ORD 기록
ord-feabebe2a95b435293adf8605180747d
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674137B2

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