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

HRID 716770ノート

反応式

HRID 716770 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d703efb77be747c99c0b4c83df235f2b
出典データセット
uspto-grants-2015_11
特許番号
US09193669B2

反応ノート

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