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

HRID 1602163Notes

Reaction equation

HRID 1602163 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0d3311ec7979493684b5d61780052a90
Source dataset
uspto-grants-1999_11
Patent number
US05981521

Reaction notes

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