Sodium sulfate decahydrate → trans-1-[2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine

HRID 1639759Notes

Reaction equation

HRID 1639759 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:22]=[C:11]2[C:12]([C@@H:16]3[CH2:18][C@H:17]3[CH:19]=[N:20]O)=[CH:13][CH:14]=[CH:15][N:10]2[N:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:7][C:8]1[CH:22]=[C:11]2[C:12]([C@@H:16]3[CH2:18][C@H:17]3[CH2:19][NH2:20])=[CH:13][CH:14]=[CH:15][N:10]2[N:9]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 86641923trans-2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarbaldehyde oxime

Product 1

HCID 59334541trans-1-[2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (1.18 g, 31.0 mmol) in tetrahydrofuran (70 mL) was added a solution of trans-2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarbaldehyde oxime (1.67 g, 7.76 mmol) in tetrahydrofuran (8 mL) at room temperature, and the mixture was stirred at room temperature for 1.5 hr. Sodium sulfate decahydrate (17 g) was added under ice-cooling, and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure to give the title compound (1.39 g, yield 89%).

Workup

  1. temperaturecooling
  2. filtrationthe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-767e125884e64b6aad13f682585799fe
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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