Aluminium lithium hydride → 1-[4-(Trifluoromethoxy)phenyl]cyclopentanemethanamine

HRID 404604Notes

Reaction equation

HRID 404604 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:24])([F:23])[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:21]#[N:22])[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1>CCOCC>[F:7][C:8]([F:23])([F:24])[O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([CH2:21][NH2:22])[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 595365491-[4-(Trifluoromethoxy)phenyl]cyclopentanecarbonitrile

Product 1

HCID 595365551-[4-(Trifluoromethoxy)phenyl]cyclopentanemethanamineYield 78.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To lithium aluminium hydride (379 mg, 10 mmol) in Et2O (10 mL) was added dropwise a solution of 1-(4-(trifluoromethoxy)phenyl)cyclopentanecarbonitrile (905 mg, 4 mmol) in Et2O (5 mL) at 0° C. The reaction mixture was stirred at room temperature under an atmosphere of nitrogen for 16 h and then quenched with saturated sodium sulfate solution (3 mL) and extracted with Et2O. The organic layer was dried with sodium sulfate and evaporated in vacuo to give (1-(4-(trifluoromethoxy)phenyl)cyclopentyl)methanamine as an oil (810 mg, 77%).

Workup

  1. customquenched with saturated sodium sulfate solution (3 mL)
  2. extractionextracted with Et2O
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ea0f80b23f1a4cddb6d79ac2e1bea628
Source dataset
uspto-grants-2014_06
Patent number
US08748612B2

Reaction notes

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