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

HRID 716792ノート

反応式

HRID 716792 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-06dbc9892d76453b8558a4eaaa315c1b
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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