Hydride → 3-Hexyl-6-methyl-6-[3-(2-pyridyl)phenyl]-3-azabicyclo[3.1.0]hexane

HRID 428859Notes

Reaction equation

HRID 428859 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH3:25])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:14]=2)[C:8]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Li].[H-]>O1CCCC1>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH3:25])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:14]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 166653HydrideHCID 3028194LithiumHCID 221412333-Hexyl-6-methyl-6-[3-(2-pyridinyl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one

Product 1

HCID 221413593-Hexyl-6-methyl-6-[3-(2-pyridyl)phenyl]-3-azabicyclo[3.1.0]hexaneYield 43.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hexyl-6-methyl-6-[3-(2-pyridinyl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one (Preparation 68, 33 mg, 0.09 mmol) was dissolved in tetrahydrofuran (10 ml) at 0° C. Lithium alumninium hydride (1M in tetrahydrofuran, 0.2 ml, 0.2 mmol) was added under nitrogen and then the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched by adding aqueous sodium hydroxide solution (2N, 0.4 ml), followed by solid sodium hydrogen carbonate and ethyl acetate. The reaction mixture was stirred vigorously and then filtered through Celite®. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate to give the product as a colourless oil (13 mg, 41%).

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding aqueous sodium hydroxide solution (2N, 0.4 ml)
  3. stirringThe reaction mixture was stirred vigorously
  4. filtrationfiltered through Celite®
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-b38da89e8ab04bdb8c3e2fe96ea4d6cd
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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