Hydrochloric Acid → N-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amine

HRID 1688865Notes

Reaction equation

HRID 1688865 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([NH2:6])=[N:2]1.[O:7]1[C:11]2([CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.[BH4-].[Na+].Cl>CO.[OH-].[Na+]>[O:7]1[C:11]2([CH2:16][CH2:15][CH:14]([NH:6][C:3]3[NH:2][N:1]=[CH:5][CH:4]=3)[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 4311764Sodium borohydrideHCID 178418806HCID 178418806, compound

Product 1

HCID 67009993N-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amineYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1H-pyrazol-3-amine (10.0 g) and 1,4-dioxaspiro[4.5]decan-8-one (20.7 g) in methanol (30 mL) was stirred at room temperature for 30 min. After stirring, a solution of sodium tetrahydroborate (3.6 g) in 1 M sodium hydroxide (30 mL) was added dropwise at 0° C. After warming to room temperature, the mixture was stirred for 4 hr, 1 M hydrochloric acid (100 mL) was added dropwise at 0° C., and the mixture was stirred for 1 hr. The resulting solid was collected by filtration, washed with water, and dried by heating under reduced pressure to give the title compound as a pale-yellow solid (17.2 g, 64%).

Workup

  1. stirringthe mixture was stirred for 4 hr
  2. stirringthe mixture was stirred for 1 hr
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customdried
  6. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-a354ff0a772243d5868e7db4a2e64e02
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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