Hydrochloric Acid → HCID 22141239, compound

HRID 428917Notes

Reaction equation

HRID 428917 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:9]=[C:10]([C:14]2([CH3:28])[CH:19]3[CH:15]2[CH2:16][N:17]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]3=O)[CH:11]=[CH:12][CH:13]=1.Cl.[OH-].[Na+]>O1CCCC1.O>[CH2:21]([N:17]1[CH2:16][CH:15]2[CH:19]([C:14]2([C:10]2[CH:9]=[C:8]([NH2:7])[CH:13]=[CH:12][CH:11]=2)[CH3:28])[CH2:18]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 22141340HCID 22141340, compound

Product 1

HCID 22141239HCID 22141239, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Lithium aluminium hydride (1M in tetrahydrofuran, 11.84 ml, 11.84 mmol) was added dropwise to dry tetrahydrofuran (60 ml) under nitrogen. 6-(3-Aninophenyl)-3-benzyl-6-methyl-3-azabicyclo[3.1.0]hexan-2-one (Preparation 29, 1.73 g, 5.90 mmol) was suspended in dry tetrahydrofuran (100 ml) and added slowly to the lithium aluminium hydride solution by cannula. The reaction was then heated at 50° C. for 2 hours. After cooling, water (20 ml) was cautiously added to the solution, the pH of the aqueous layer was adjusted to 4 by the addition of 2N hydrochloric acid and then adjusted to 10 using dilute sodium hydroxide solution. The mixture was extracted with ethyl acetate (3×200 ml), and the combined extracts were washed with water (100 ml), dried (Na2SO4) and concentrated in vacuo to give the title compound as a yellow oil (1.58 g, 96%).

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with ethyl acetate (3×200 ml)
  3. washthe combined extracts were washed with water (100 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a205929841d149c096cd13664498bd1f
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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