Ethyl 6-cyano-4,4-diphenylhexanoate → 7-Amino-4.4-diphenylheptan-1-ol

HRID 1602163ノート

反応式

HRID 1602163 の反応式
[C:1]([CH2:3][CH2:4][C:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][CH2:7][C:8](OCC)=[O:9])#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:2][CH2:1][CH2:3][CH2:4][C:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][CH2:7][CH2:8][OH:9]

参加物

4

反応物 2

HCID 19610260Ethyl 6-cyano-4,4-diphenylhexanoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 196102827-Amino-4.4-diphenylheptan-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 6-cyano-4,4-diphenyl-hexanoate (5.476 g) in anhydrous THF (195 mL) was added portionwise lithium aluminum hydride (LAH) (1.686 g). A large evolution of gas was observed. The mixture was stirred at rt for 1.5 hr. The reaction mixture was quenched by a careful addition of water (4.5 mL), followed by IN NaOH (4.5 mL) and additional water (15 niL). The mixture was stirred at rt for 10 min and then filtered and the solid was washed three times with THF. The organic filtrates were combined, dried (Na2SO4) and concentrated to give the desired product as a solid foam (4.56 g): MS showed (M+H)+ @ 284; 1H-NMR (CDCl3, δ): 1.05-1.3 (m, 4H), 2.0-2.20 (m, 4H), 2.30-2.42 (t, 2H), 2.82-3.0 (t, 2H), 3.0-3.25 (m, 2H), 3.50-3.65 (t, 2H), 5.10-5.20 (broad m, 1H), 6.86-7.36 (m, 14H).

後処理

  1. customThe reaction mixture was quenched by a careful addition of water (4.5 mL)
  2. stirringThe mixture was stirred at rt for 10 min
  3. filtrationfiltered
  4. washthe solid was washed three times with THF
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-0d3311ec7979493684b5d61780052a90
出典データセット
uspto-grants-1999_11
特許番号
US05981521

反応ノート

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