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

HRID 1602163노트

반응식

HRID 1602163 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0d3311ec7979493684b5d61780052a90
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05981521

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