Water → N-(3-{6-Methyl-3-[3-(3-thienyl)propyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

HRID 428887Notes

Reaction equation

HRID 428887 reaction equation
[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([C:8](=O)[CH2:9][CH2:10][C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)[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:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)[CH2:6]2

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 22141237N-(3-{6-methyl-3-[3-(3-thienyl)propanoyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

Product 1

HCID 22141148N-(3-{6-Methyl-3-[3-(3-thienyl)propyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamideYield 56.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-{6-methyl-3-[3-(3-thienyl)propanoyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 126, 200 mg, 0.49 mmol) in anhydrous tetrahydrofuran (7.5 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.99 ml, 0.99 mmol) and the mixture was stirred at room temperature for 2 h. The rapidly stirred reaction mixture was treated sequentially with water (1 ml), sodium hydrogen carbonate (1.0 g) and ethyl acetate (25 ml). After 15 min the reaction mixture was filtered and concentrated in vacuo to afford a light yellow oil. This was purified by chromatography using a Biotage Flash 12™ cartridge packed with silica gel (8 g) eluting with hexane:ethyl acetate (100:0 to 0:100) to afford the title compound as a colourless oil (108 mg, 56%).

Workup

  1. customThe rapidly stirred reaction mixture
  2. filtrationAfter 15 min the reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customto afford a light yellow oil
  5. customThis was purified by chromatography
  6. washeluting with hexane:ethyl acetate (100:0 to 0:100)

Sources & evidence

ORD record
ord-d00e82b4d43246468df89d7ab4f2f93f
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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