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

HRID 716770노트

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HRID 716770 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-d703efb77be747c99c0b4c83df235f2b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193669B2

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