Aluminium lithium hydride → HCID 67453361, compound

HRID 1853119Notes

Reaction equation

HRID 1853119 reaction equation
[F:1][C:2]1[C:3]([C:8]2([C:12]#[N:13])[CH2:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[C:3]([C:8]2([CH2:12][NH2:13])[CH2:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 674528781344145-52-3

Product 1

HCID 67453361HCID 67453361, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 1-(3-fluoropyridin-2-yl)cyclobutanecarbonitrile (88 g, 500 mmol, 1.0 equiv) in THF (400 mL) was added LAH (2M in THF, 575 mL, 1.15 mol) in a dropwise manner over one hour. The reaction was then warmed to room temperature and stirred for 15 min. After the reaction was complete, it was cooled back down to 0° C. and quenched slowly with water (43 mL), 3 N NaOH (43 mL), and water (125 mL). The quenched reaction was stirred for 30 min and then filtered through Celite. The filtrate was concentrated and dried in vacuo to give (1-(3-fluoropyridin-2-yl)cyclobutyl)methanamine (80 g, 88%) as a crude yellow oil that was used without purification.

Workup

  1. temperatureit was cooled back down to 0° C.
  2. customquenched slowly with water (43 mL), 3 N NaOH (43 mL), and water (125 mL)
  3. customThe quenched reaction
  4. stirringwas stirred for 30 min
  5. filtrationfiltered through Celite
  6. concentrationThe filtrate was concentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-cd141c1165d041a6ad9e64482147b4b9
Source dataset
uspto-grants-2015_02
Patent number
US08962632B2

Reaction notes

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