Aluminium lithium hydride → HCID 90409494, compound

HRID 1484785Notes

Reaction equation

HRID 1484785 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][CH2:11][C:10]=2[C:22](OCC)=[O:23])=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:23][CH2:22][C:10]1[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:14][C:9]=1[C:8]1[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90407833HCID 90407833, compound

Product 1

HCID 90409494HCID 90409494, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 1-(tert-butyl) 4-ethyl 5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydropyridine-1,4(2H)-dicarboxylate (450 mg, 1.24 mmol) in THF (6 mL) was added LiAlH4 (1M in THF, 1.49 mL, 1.49 mmol) at −20° C., the reaction was stirred at −20° C. for 30 min, and was quenched with Sat. NH4Cl, the aqueous layer was extracted with EtOAc, the combined organics were washed with brine, dried and concentrated to give crude oil, which was purified by column (Hexanes/EtOAc=100:0 to 40:60) to give tert-butyl 4-(hydroxymethyl)-5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydropyridine-1(2H)-carboxylate (370 mg, 91%).

Workup

  1. customwas quenched with Sat. NH4Cl
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washthe combined organics were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give crude oil, which
  7. customwas purified by column (Hexanes/EtOAc=100:0 to 40:60)

Sources & evidence

ORD record
ord-512aaf07899746d7bd48ae987d773f82
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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