Water → HCID 22141255, compound

HRID 428884Notes

Reaction equation

HRID 428884 reaction equation
[CH3:1][C:2]1([C:20]2[CH:21]=[C:22]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:23]=[CH:24][CH:25]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([C:8](=O)[CH2:9][C:10]([CH3:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11])[CH2:6]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1([C:20]2[CH:21]=[C:22]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:23]=[CH:24][CH:25]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][C:10]([CH3:11])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:18])[CH2:6]2

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 22141353HCID 22141353, compound

Product 1

HCID 22141255HCID 22141255, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{3-[6-methyl-3-(3-methyl-3-phenylbutanoyl)-3-azabicyclo[3.1.0]hex-6-yl]phenyl}methanesulfonamide (Preparation 122, 59 mg, 0.138 mmol) in anhydrous tetrahydrofuran (1 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.28 ml, 0.28 mmol) and the mixture was stirred at room temperature for 3 h. The rapidly stirred reaction mixture was treated sequentially with water (0.28 ml), sodium hydrogen carbonate (200 mg) and ethyl acetate (10 ml). After 30 min the reaction mixture was filtered and concentrated in vacuo to afford a pale yellow oil. This was purified by preparative HPLC (condition 8) to give a light brown oil which was partitioned between dichloromethane (15 ml) and aqueous potassium carbonate solution (7% w:v, 5 ml). The layers were separated and the organic layer was washed with water (5 ml), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a colourless oil (38 mg, 66%).

Workup

  1. customThe rapidly stirred reaction mixture
  2. filtrationAfter 30 min the reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customto afford a pale yellow oil
  5. customThis was purified by preparative HPLC (condition 8)
  6. customto give a light brown oil which
  7. customwas partitioned between dichloromethane (15 ml) and aqueous potassium carbonate solution (7% w:v, 5 ml)
  8. customThe layers were separated
  9. washthe organic layer was washed with water (5 ml)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e53fc6e750af4e0d8791a262c9edf685
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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